Synergistic herbicidal composition containing certain pyridine or pyrimidine carboxylic acids and certain cereal and rice herbicides

ABSTRACT

An herbicidal composition containing (a) a pyridine or pyrimidine carboxylic acid component and (b) a second cereal or rice herbicide component provides synergistic control of selected weeds.

This application claims the benefit of U.S. Provisional Application 60/966,340 filed Aug. 27, 2007.

FIELD OF THE INVENTION

This invention concerns a synergistic herbicidal composition containing (a) an herbicidal pyridine or pyrimidine carboxylic acid component and (b) a cereal or rice herbicide component.

BACKGROUND OF THE INVENTION

The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use.

In some cases, herbicidal active ingredients have been shown to be more effective in combination than when applied individually and this is referred to as “synergism.” As described in the Herbicide Handbook of the Weed Science Society of America, Seventh Edition, 1994, p. 318, “‘synergism’ [is] an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response of each factor applied separately.” The present invention is based on the discovery that certain cereal or rice herbicides and certain pyridine or pyrimidine carboxylic acids, already known individually for their herbicidal efficacy, display a synergistic effect when applied in combination.

The herbicidal compounds forming the synergistic composition of this invention are independently known in the art for their effects on plant growth.

SUMMARY OF THE INVENTION

The present invention concerns a synergistic herbicidal mixture comprising an herbicidally effective amount of (a) a first herbicide selected from the group of a pyridine or a pyrimidine carboxylic acid of the formula (I)

-   -   wherein X represents CH or N, hal represents F, Cl or Br, and R         represents methyl or ethyl,         and agriculturally acceptable salts, esters and amides of the         carboxylic acid, and (b) a second herbicide selected from the         group consisting of amidosulfuron, aminopyralid, beflubutamid,         bensulfuron, bentazone, bispyribac, bromoxynil, carfentrazone,         chlormequat, chlorsulfuron, chlorotoluron, clodinafop,         clomazone, cyhalofop, dicamba, dichlorprop, diflufenican,         diflufenzopyr, fenoxaprop, florasulam, flucarbazone, flufenacet,         flupyrsulfuron, halosulfuron, indol-3-ylacetic acid,         4-indol-3-ylbutyric acid, imazamethabenz, imazamox, imazethapyr,         iodosulfuron, isoproturon, isoxaben, MCPA, mesosulfuron,         metribuzin, metsulfuron, norflurazon, penoxsulam, picolinafen,         pinoxaden, propanil, propoxycarbazone, prosulfocarb,         pyrasulfotole, pyrazosulfuron, pyriclor, pyroxsulam, quinclorac,         sulcotrione, sulfosulfuron, thifensulfuron, tralkoxydim,         tribenuron, triclopyr and mixtures thereof. The compositions may         also contain an agriculturally acceptable adjuvant or carrier.         The synergistic compositions may also generally be employed in         combination with known herbicide safeners, particularly with         cloquintocet mexyl.

Compounds of formula (I) in which X represents CH or N, hal represents F or Cl, and R represents methyl are independently preferred.

The present invention also concerns herbicidal compositions for and methods of controlling the growth of undesirable vegetation, particularly in wheat, rye, barley, oats, triticale and rice, and the use of these synergistic compositions.

The species spectra of the compounds of the synergistic mixture, i.e., the weed species which the respective compounds control, are broad and highly complimentary. For example, it has been surprisingly found that a combination of diflufenican, optionally with flufenacet, and a pyridine or pyrimidine carboxylic acid of the formula (I) exhibits a synergistic action in the control of blackgrass (Alopecurus myosuroides L; ALOMY), windgrass (Apera spica-venti L; APESV), wild oats (Avena fatua L; AVEFA), annual ryegrass (Lolium multiflorum L; LOLMG), lamb's-quarters (Chenopodium album L; CHEAL), wild mustard (Sinapis arvensis L SINAR), chickweed (Stellaria media L; STEME), scented mayweed (Matricaria chamomila L; MATCH) at application rates lower than the rates of the individual compounds.

It has also been surprisingly found that a mixture of an acetyl coenzyme A carboxylase-inhibiting herbicide such as clodinafop, fenoxaprop-P, pinoxaden or tralkoxydim, and a pyridine or pyrimidine carboxylic acid of the formula (I) exhibits a synergistic action in control of blackgrass (Alopecurus myosuroides L; ALOMY), windgrass (Apera spica-venti L; APESV), wild oats (Avena fatua L; AVEFA), annual ryegrass (Lolium multiflorum L; LOLMG), littleseed Canarygrass (Phalaris minor L; PHAMI) at application rates lower than the rates of the individual compounds.

The mixtures of an acetolactate synthase-inhibitor herbicide such as flupyrsulfuron, iodosulfuron, mesosulfuron, mesosulfuron plus iodosulfuron or sulfosulfuron of the sulfonylureas class; imazamethabenz of the imidazolinones class; propoxycarbazone of the sulfonylaminocarbonyltriazolinones class; pyroxsulam of the triazolopyrimidine class; and a pyridine or pyrimidine carboxylic acid of the formula (I) unexpectedly exhibit a synergistic action in control of blackgrass (Alopecurus myosuroides L; ALOMY), windgrass (Apera spica-venti L; APESV), wild oats (Avena fatua L; AVEFA), downy brome (Bromus tectorum L; BROTE), annual ryegrass (Lolium multiflorum L; LOLMG), Italian ryegrass (Lolium multiflorum L; LOLMU), rigid ryegrass (Lolium rigidum L; LOLRI), littleseed Canarygrass (Phalaris minor L; PHAMI), yellow foxtail (Pennisetum americanum L; PESGL), annual bluegrass (Poa annua L; POAAN), green foxtail (Setaria viridis L; SETVI) at application rates lower than the rates of the individual compounds.

It has also been unexpectedly found that the mixture of an acetolactate synthase inhibiting herbicide such as amidosulfuron, chlorsulfuron, flupyrsulfuron, iodosulfuron, mesosulfuron, mesosulfuron plus iodosulfuron, metsulfuron, sulfosulfuron, thifensulfuron or tribenuron of the sulfonylureas class; propoxycarbazone or flucarbazone of the sulfonylaminocarbonyl-triazolinone class; imazamethabenz of the imidazolinones class; florasulam or pyroxsulam of the triazolopyrimidines class; and a pyridine or pyrimidine carboxylic acid of the formula (I) shows a synergistic action in control of canola (Brassica napus L; BRSNN), Canada thistle (Cirsium arvense L; CIRAR), chickweed (Stellaria media L; STEME), scented mayweed (Matricaria chamomila L; MATCH), bird's-eye speedwell (Veronica persica L; VERPE), wild pansy (Viola tricolor L; VIOTR), lady's-thumb (Polygonum persicaria L; POLPE), kochia (Kochia scoparia L; KCHSC) at application rates lower than the rates of the individual compounds.

The combination of a phytoene desaturase-inhibiting herbicide such as beflubutamid or picolinafen, and a pyridine or pyrimidine carboxylic acid of the formula (I) has resulted in an unexpected synergistic action in the control of kochia (Kochia scoparia L; KCHSC), wild mustard (Sinapis arvensis L; SINAR), ivy-leaved speedwell (Veronica hederifolia L; VERHE), bird's-eye speedwell (Veronica persica L; VERPE), wild pansy (Viola tricolor L; VIOTR), black mustard (Brassica nigra L; BRSNI), cut-leaf geranium (Geranium dissectum L; GERDI), wild buckwheat (Polygonum convolvulus L; POLCO), lady's-thumb (Polygonum persicaria L; POLPE), chickweed (Stellaria media L; STEME) at application rates lower than the rates of the individual compounds.

Surprisingly, the combinations of photosystem II-inhibiting herbicides such as bentazone, bromoxynil, chlorotoluron, isoproturon or metribuzin, and a pyridine or pyrimidine carboxylic acid of the formula (I) show a synergistic action in control of black mustard (Brassica nigra L; BRSNI), wild buckwheat (Polygonum convolvulus L; POLCO), chickweed (Stellaria media L; STEME), scented mayweed (Matricaria chamomila L; MATCH), bird's-eye speedwell (Veronica persica L; VERPE), wild pansy (Viola tricolor L; VIOTR), kochia (Kochia scoparia L; KCHSC), Russian thistle (Salsola iberica L; SASKR) at application rates lower than the rates of the individual compounds. It has been also surprisingly found that a combination of bromoxynil, optionally with pyrasulfotole, and a pyridine or pyrimidine carboxylic acid of the formula (I) shows a synergistic action in control of scented mayweed (Matricaria chamomila L; MATCH), bird's-eye speedwell (Veronica persica L; VERPE), wild pansy (Viola tricolor L; VIOTR), kochia (Kochia scoparia L; KCHSC) at application rates lower than the rates of the individual compounds.

The combination of a plant growth regulator such as chlormequat, indol-3-ylacetic acid or 4-indol-3-ylbutyric acid, and a pyridine or pyrimidine carboxylic acid of the formula (I) has resulted in an unexpected synergistic action in the control of kochia (Kochia scoparia L; KCHSC), black mustard (Brassica nigra L; BRSNI), cut-leaf geranium (Geranium dissectum L; GERDI), wild buckwheat (Polygonum convolvulus L; POLCO), chickweed (Stellaria media L; STEME), scented mayweed (Matricaria chamomila L; MATCH) at application rates lower than the rates of the individual compounds. Similarly, the mixtures of isoxaben, a cell wall biosynthesis inhibiting herbicide, or prosulfocarb, a lipid biosynthesis inhibiting herbicide, and a pyridine or pyrimidine carboxylic acid of the formula (I) have resulted in an unexpected synergistic action in the control of black mustard (Brassica nigra L; BRSNI), chickweed (Stellaria media L; STEME), scented mayweed (Matricaria chamomila L; MATCH), bird's-eye speedwell (Veronica persica L; VERPE), wild pansy (Viola tricolor L; VIOTR), Russian thistle (Salsola iberica L; SASKR) at application rates lower than the rates of the individual compounds.

It has also been unexpectedly found that the mixture of an auxinic herbicide such as aminopyralid, optionally with picolinafen or diflufenican, dicamba, dichlorprop-P, MCPA, quinclorac and a pyridine or pyrimidine carboxylic acid of the formula (I) exhibits a synergistic action in control of chickweed (Stellaria media L; STEME), scented mayweed (Matricaria chamomila L; MATCH), bird's-eye speedwell (Veronica persica L; VERPE), wild pansy (Viola tricolor L; VIOTR), lady's-thumb (Polygonum persicaria L; POLPE), kochia (Kochia scoparia L; KCHSC), black mustard (Brassica nigra L; BRSNI), cut-leaf geranium (Geranium dissectum L; GERDI), wild buckwheat (Polygonum convolvulus L; POLCO) at application rates lower than the rates of the individual compounds.

It has been also surprisingly found that the mixture of an EPSP (5-enolpyruvylshikimate-3-phosphate) synthase inhibitor herbicide such as glyphosate and a pyridine or pyrimidine carboxylic acid of the formula (I) exhibits a synergistic action in control of wild pansy (Viola tricolor L; VIOTR), kochia (Kochia scoparia L; KCHSC), Russian thistle (Salsola iberica L; SASKR) at application rates lower than the rates of the individual compounds.

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid and 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)-pyrimidine-4-carboxylic acid derivatives are the especially preferred pyridine or pyrimidine carboxylic acids of the formula (I) for the control of weeds in cereal crops including spring, winter and durum wheat, spring and winter barley, oats, and triticale.

In rice culture (direct seeded, water seeded, or transplanted), the combination of an acetolactate synthase (ALS)-inhibiting herbicide such as penoxsulam of the triazolopyrimidine class; bispyribac-sodium of the pyrimidinylbenzoate chemical class; bensulfuron-methyl, halosulfuron-methyl, or pyrazosulfuron-ethyl of the sulfonylurea chemical class; or imazethapyr or imazamox of the imidazolinone chemical class; and a pyridine carboxylic acid of the formula (I) has resulted in an unexpected synergistic action in the control of Ipomoea hederacea (L.) JACQ. (IPOHE), Echinochloa species (ECHSS), Ischaemum rugosum SALISB. (ISCRU), Leptochloa chinensis (L.) NEES (LEFCH), Cyperus esculentus L. (CYPES), Cyperus iria L. (CYPIR), and Eleocharis kuroguwai OHWI (ELOKU) at application rates lower than the rates of the individual compounds. Glyphosate, an amino acid biosynthesis inhibitor which specifically inhibits 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase, in combination with a pyridine carboxylic acid of the formula (I), produces synergistic activity on Polygonum pensylvanicum L. (POLPY), CYPES, CYPIR, Digitaria sanguinalis (L.) SCOP. (DIGSA), and LEFCH at application rates lower than the rates of the individual compounds. Synergistic activity between pyridine carboxylic acids of the formula (I) in combination with compounds of the imidazolinone chemistry class or in combination with glyphosate will be particularly useful in crops where imidazolinone or glyphosate resistant crop varieties are being employed.

It has also been surprising that a mixture of propanil, a photosystem (PS) II-inhibiting herbicide and a pyridine carboxylic acid of the formula (I) exhibits a synergistic action in control of IPOHE and Polygonum persicaria L. (POLPE), at application rates lower than the rates of the individual compounds and an increased speed of activity on CYPIR and Scirpus maritimus L. (SCPMA) over that observed with effective control rates of the individual compounds. Similarly, a mixture of carfentrazone-ethyl, a protoporphyrinogen IX oxidase (PROTOX) inhibiting herbicide, and a pyridine carboxylic acid of the formula (I) exhibits a synergistic action in control POLPE, CYPES, and CYPIR at application rates lower than the rates of the individual compounds as well as an increased speed of activity on CYPES.

It has also been unexpectedly found that the mixture of cyhalofop-butyl, an acetyl coenzyme A carboxylase (ACCase) inhibiting herbicide, and a pyridine carboxylic acid of the formula (I) shows a synergistic action in the control of POLPY, Sphenoclea zeylanica GAERTN. (SPDZE), ECHSS, LEFCH, Cyperus species (CYPSS), Fimbristylis miliacea (L.) VAHL (FIMMI), and Scirpus species (SCPSS) at application rates lower than the rates of the individual compounds, while a mixture of fenoxaprop-p-ethyl, another ACCase-inhibiting herbicide, and a pyridine carboxylic acid of the formula (I) shows a synergistic action in control of FIMMI and SCPSS at application rates lower than the rates of the individual compounds.

The combination of an auxinic herbicide such as triclopyr, MCPA, or quinclorac and a pyridine carboxylic acid of the formula (I) has resulted in an unexpected synergistic action in the control of Marsilea crenata PRESL (MASCR), CYPSS, FIMMI, ECHSS, LEFCH, Brachiaria platyphylla (BRISEB.) NASH (BRAPP), and ISCRU at application rates lower than the rates of the individual compounds. Similarly, the combination of an auxin transport inhibitor such as diflufenzopyr and a pyridine carboxylic acid of the formula (I) has resulted in an unexpected synergistic action in the control of IPOHE, LEFCH, and CYPIR at application rates lower than the rates of the individual compounds.

The combination of compounds with bleaching modes of action such as clomazone; norflurazon, a phytoene desaturase inhibiting herbicide; sulcotrione, a p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting herbicide; or pyriclor and a pyridine carboxylic acid of the formula (I) has resulted in an unexpected synergistic action in the control of BRAPP, DIGSA, ECHSS, LEFCH, CYPSS, FIMMI, and SCPMA at application rates lower than the rates of the individual compounds.

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid derivatives, 4-amino-3-chloro-6-(2,4-dichloro-3-methoxyphenyl)-pyridine-2-carboxylic acid derivatives, and 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-ethoxyphenyl)pyridine-2-carboxylic acid derivatives are the especially preferred pyridine carboxylic acids of the formula (I) for the control of weeds in transplanted, water seeded, and direct seeded rice.

DETAILED DESCRIPTION OF THE INVENTION

The pyridine and pyrimidine carboxylic acids are a new class of compounds having herbicidal activity. A number of pyridine and pyrimidine carboxylic acid compounds are described in U.S. Pat. Nos. 7,300,907 (B2) and 7,314,849 (B2), including 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid methyl ester and 4-amino-3-chloro-6-(2,4-dichloro-3-methoxyphenyl)pyridine-2-carboxylic acid methyl ester. The pyridine or pyrimidine carboxylic acid of the formula (I) controls annual grass weeds including Setaria, Pennisetum, and Echinochloa; broadleaf weeds such as Papaver, Galium, Lamium, Kochia, Amaranthus, Aeschynomene, Sesbania, and Monochoria; and sedge species such as Cyperus and Scirpus.

Amidosulfuron is the common name for N-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N-methylmethanesulfonamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Amidosulfuron controls a wide range of broadleaf weeds, particularly cleavers.

Aminopyralid is the common name for 4-amino-3,6-dichloro-2-pyridinecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Aminopyralid controls annual and perennial broadleaf weeds in grassland.

Beflubutamid is the common name for 2-[4-fluoro-3-(trifluoromethyl)-phenoxy]-N-(phenylmethyl)butanamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Beflubutamid provides pre- and early post-emergence control of broadleaf weeds in wheat and barley.

Bensulfuron is the common name for 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Bensulfuron-methyl controls annual and perennial weeds and sedges in flooded or wetland rice.

Bentazone is the common name for 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Bentazone controls broadleaf weeds in spring and winter cereals.

Bispyribac is the common name for 2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Bispyribac-sodium controls grasses, sedges and broadleaf weeds in direct-seeded rice.

Bromoxynil is the common name for 3,5-dibromo-4-hydroxybenzonitrile. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Bromoxynil is used for the post-emergence control of annual broadleaf weeds.

Carfentrazone is the common name for α,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorobenzenepropanoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Carfentrazone-ethyl controls a wide range of broadleaf weeds in cereals and rice.

Chlormequat is the common name for 2-chloro-N,N,N-trimethyl-ethanaminium chloride. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Chlormequat is a plant growth regulator for producing sturdier plants.

Chlorsulfuron is the common name for 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Chlorsulfuron controls a wide range of broadleaf weeds and some annual grasses.

Chlorotoluron is the common name for N′-(3-chloro-4-methylphenyl)-N,N-dimethylurea. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Chlorotoluron controls a wide range of broadleaf weeds and some annual grasses in winter cereals.

Clodinafop is the common name for (2R)-2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Clodinafop controls a wide range of annual grasses.

Clomazone is the common name for 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Clomazone controls grass weeds and broadleaf weeds.

Cyhalofop is the common name for (2R)-2-[4-(4-cyano-2-fluorophenoxy)-phenoxy]propanoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Cyhalofop-butyl controls grass weeds in rice.

Dicamba is the common name for 3,6-dichloro-2-methoxybenzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Dicamba controls annual and perennial broadleaf weeds in cereals.

Dichlorprop P is the common name for (2R)-2-(2,4-dichlorophenoxy)propanoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Dichlorprop controls a wide range of annual and perennial broadleaf weeds in cereals and grassland.

Diflufenican is the common name for N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]-3-pyridinecarboxamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Diflufenican controls annual grass weeds and certain broadleaf weeds including Galium, Veronica and Viola spp.

Diflufenzopyr is the common name for 2-[1-[[[(3,5-difluorophenyl)-amino]carbonyl]hydrazono]ethyl]-3-pyridinecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Diflufenzopyr controls annual and perennial broadleaf weeds.

Fenoxaprop is the common name for 2-[4-[(6-chloro-2-benzoxazolyl)-oxy]phenoxy]propanoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Fenoxaprop controls a wide range of annual and perennial grasses.

Florasulam is the common name for N-(2,6-difluorophenyl)-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Florasulam controls broadleaf weeds, especially Galium aparine, Stellaria media, Polygonum convolvulus, Matricaria spp. and various cruciferae.

Flucarbazone is the common name for 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2-(trifluoromethoxy)phenyl]sulfonyl]-1H-1,2,4-triazole-1-carboxamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Flucarbazone controls grass weeds, especially Avena fatua and Setaria viridis and some broadleaf weeds.

Flufenacet is the common name for N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Flufenacet controls a broad spectrum of grass weeds and certain broadleaf weeds.

Flupyrsulfuron is the common name for 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifluoromethyl)-3-pyridinecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Flupyrsulfuron controls black-grass and some broadleaf weeds.

Glyphosate is the common name for N-(phosphonomethyl)glycine. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Glyphosate controls a wide range of annual and perennial, broadleaf and grass weeds.

Halosulfuron is the common name for 3-chloro-5-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrazole-4-carboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Halosulfuron-methyl controls annual broadleaf weeds and nutsedge in rice.

Imazamethabenz is the common name for 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(or 5)-methylbenzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Imazamethabenz controls Alopecurus, Apera and Avena in wheat, barley and rye.

Imazamox is the common name for 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-(methoxymethyl)-3-pyridinecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Imazamox is used for broad spectrum weed control in a variety of crops.

Imazethapyr is the common name for 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Imazethapyr controls annual and perennial grass and broadleaf weeds.

Indol-3-ylacetic acid is the common name for 1H-indole-3-acetic acid. Its plant growth regulating activity is described in The Pesticide Manual, Fourteenth Edition, 2006.

4-Indol-3-ylbutyric acid is the common name for 1H-indole-3-butanoic acid. Its plant growth regulating activity is described in The Pesticide Manual, Fourteenth Edition, 2006.

Iodosulfuron is the common name for 4-iodo-2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Iodosulfuron controls grass and broadleaf weeds.

Isoproturon is the common mane for N,N-dimethyl-N′-[4-(1-methylethyl)phenyl]urea. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Isoproturon controls a wide range of annual broadleaf and grass weeds in cereals other than durum wheat.

Isoxaben is the common name for N-[3-(1-ethyl-1-methylpropyl)-5-isoxazolyl]-2,6-dimethoxybenzamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Isoxaben pre-emergently controls broadleaf weeds in cereals.

MCPA is (4-chloro-2-methylphenoxy)acetic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. MCPA controls annual and perennial broadleaf weeds in crops including cereals.

Mesosulfuron is the common name for 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-[[(methylsulfonyl)amino]-methyl]benzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Mesosulfuron controls grass and some broadleaf weeds.

Metribuzin is the common name for 4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Metribuzin controls many grasses and broadleaf weeds in cereals.

Metsulfuron is the common name for 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yeamino]carbonyl]amino]sulfonyl]benzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Metsulfuron controls a wide range of grass and broadleaf weeds in wheat, barley, rice and oats.

Norflurazon, is the common name for 4-chloro-5-(methylamino)-2-[3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Norflurazon is used for the pre-emergence control of grasses and sedges, as well as some broadleaf weeds.

Penoxsulam is the common name for 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)-benzenesulfonamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Penoxsulam controls broadleaf, sedge, and aquatic weeds and Echinochloa spp. in rice.

Picolinafen is the common name for N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]-2-pyridinecarboxamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Picolinafen controls broadleaf weeds, especially Galium, Viola, Lamium and Veronica spp.

Pinoxaden is the common name for 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl 2,2-dimethylpropanoate. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Pinoxaden controls annual grasses, including Alopecurus, Apera, Avena, Lolium, Phalaris and Setaria.

Propanil is the common name for N-(3,4-dichlorophenyl)propanamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Propanil controls grass and broadleaf weeds in rice.

Propoxycarbazone is the common name for methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]benzoate. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Propoxycarbazone controls annual and some perennial grasses, including Bromus spp., Alopecurus myosuroides, Apera spica-venti, and Elymus repens, and some broadleaf weeds.

Prosulfocarb is the common name for S-(phenylmethyl) dipropylcarbamo-thioate. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Prosulfocarb controls a wide range of grass and broadleaf weeds in wheat, barley and rye.

Pyrasulfotole is the common name for (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone. Pyrasulfotole controls a broad spectrum of broadleaf weeds in cereals.

Pyrazosulfuron is the common name for 5-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrazole-4-carboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Pyrazosulfuron-ethyl controls annual and perennial broadleaf weeds and sedges in rice.

Pyriclor is the common name for 2,3,5-trichloro-4-pyridinol.

Pyroxsulam is the common name for N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)-3-pyridinesulfonamide Pyroxsulam controls grass and broadleaf weeds.

Quinclorac is the common name for 3,7-dichloro-8-quinolinecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Quinclorac controls weeds in transplanted and direct-seeded rice.

Sulcotrione is the common name for 2-[2-chloro-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Sulcotrione controls grass and broadleaf weeds.

Sulfosulfuron is the common name for N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-2-(ethylsulfonyl)imidazo[1,2-a]pyridine-3-sulfonamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Sulfosulfuron controls annual grasses and broadleaf weeds.

Thifensulfuron is the common name for 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yeamino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Thifensulfuron controls a wide range of annual weeds.

Tralkoxydim is the common name 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1-one. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Tralkoxydim controls annual grasses, including Avena spp., Lolium spp., Setaria viridis, Phalaris spp., Alopecurus myosuroides and Apera spica-venti.

Tribenuron is the common name 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yemethylamino]carbonyl]amino]sulfonyl]benzoic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Tribenuron controls broadleaf weeds.

Triclopyr is the common name for [(3,5,6-trichloro-2-pyridinyl)oxy]acetic acid. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Triclopyr controls broadleaf weeds in rice.

The term herbicide is used herein to mean an active ingredient that kills, controls or otherwise adversely modifies the growth of plants. An herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation, and the like. The terms plants and vegetation include germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation.

Herbicidal activity is exhibited by the compounds of the synergistic mixture when they are applied directly to the plant or to the locus of the plant at any stage of growth or before planting or emergence. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted as is known in the art to promote non-selective or selective herbicidal action. Generally, it is preferred to apply the composition of the present invention postemergence to relatively immature undesirable vegetation to achieve the maximum control of weeds.

In the composition of this invention, the weight ratio of the pyridine or pyrimidine carboxylic acid of formula (I) component to the second cereal or rice herbicide component at which the herbicidal effect is synergistic lies within the range of between about 5:1 and about 1:256.

The rate at which the synergistic composition is applied will depend upon the particular type of weed to be controlled, the degree of control required, and the timing and method of application. In general, the composition of the invention can be applied at an application rate of between about 8 grams per hectare (g/ha) and about 1200 g/ha based on the total amount of active ingredients in the composition. Depending upon the particular cereal or rice herbicide used, the cereal or rice herbicide component is applied at a rate between about 4 g/ha and about 1120 g/ha and the pyridine or pyrimidine carboxylic acid of formula (I) component is applied at a rate between about 4 g/ha and about 70 g/ha

The components of the synergistic mixture of the present invention can be applied either separately or as part of a multipart herbicidal system.

The synergistic mixture of the present invention can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the synergistic composition of the present invention include: amide herbicides such as allidochlor, benzadox, benzipram, bromobutide, cafenstrole, CDEA, chlorthiamid, cyprazole, dimethenamid, dimethenamid-P, diphenamid, epronaz, etnipromid, fentrazamide, flupoxam, fomesafen, halosafen, isocarbamid, napropamide, naptalam, pethoxamid, propyzamide, quinonamid and tebutam; anilide herbicides such as chloranocryl, cisanilide, clomeprop, cypromid, etobenzanid, fenasulam, flufenican, mefenacet, mefluidide, metamifop, monalide, naproanilide and pentanochlor; arylalanine herbicides such as benzoylprop, flamprop and flamprop-M; chloroacetanilide herbicides such as acetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor and xylachlor; sulfonanilide herbicides such as benzofluor, perfluidone, pyrimisulfan and profluazol; sulfonamide herbicides such as asulam, carbasulam, fenasulam and oryzalin; antibiotic herbicides such as bilanafos; benzoic acid herbicides such as chloramben, 2,3,6-TBA and tricamba; pyrimidinyloxybenzoic acid herbicides such as pyriminobac; pyrimidinylthiobenzoic acid herbicides such as pyrithiobac; phthalic acid herbicides such as chlorthal; picolinic acid herbicides such as clopyralid and picloram; quinolinecarboxylic acid herbicides such as quinmerac; arsenical herbicides such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite; benzoylcyclohexanedione herbicides such as mesotrione, tefuryltrione and tembotrione; benzofuranyl alkylsulfonate herbicides such as benfuresate and ethofumesate; carbamate herbicides such as asulam, carboxazole chlorprocarb, dichlormate, fenasulam, karbutilate and terbucarb; carbanilate herbicides such as barban, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, desmedipham, phenisopham, phenmedipham, phenmedipham-ethyl, propham and swep; cyclohexene oxime herbicides such as alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim and tepraloxydim; cyclopropylisoxazole herbicides such as isoxachlortole and isoxaflutole; dicarboximide herbicides such as benzfendizone, cinidon-ethyl, flumezin, flumiclorac, flumioxazin and flumipropyn; dinitroaniline herbicides such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin and trifluralin; dinitrophenol herbicides such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen and medinoterb; diphenyl ether herbicides such as ethoxyfen; nitrophenyl ether herbicides such as acifluorfen, aclonifen, bifenox, chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen,nitrofen, nitrofluorfen and oxyfluorfen; dithiocarbamate herbicides such as dazomet and metam; halogenated aliphatic herbicides such as alorac, chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA and TCA; imidazolinone herbicides such as imazapic, imazapyr and imazaquin; inorganic herbicides such as ammonium sulfamate, borax, calcium chlorate, copper sulfate, ferrous sulfate, potassium azide, potassium cyanate, sodium azide, sodium chlorate and sulfuric acid; nitrile herbicides such as bromobonil, chloroxynil, dichlobenil, iodobonil, ioxynil and pyraclonil; organophosphorus herbicides such as amiprofos-methyl, anilofos, bensulide, bilanafos, butamifos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glyphosate and piperophos;

phenoxy herbicides such as bromofenoxim, clomeprop, 2,4-DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid, fenteracol and trifopsime; phenoxyacetic herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA-thioethyl and 2,4,5-T; phenoxybutyric herbicides such as 4-CPB, 2,4-DB, 3,4-DB, MCPB and 2,4,5-TB; phenoxypropionic herbicides such as cloprop, 4-CPP, 3,4-DP, fenoprop, mecoprop and mecoprop-P; aryloxyphenoxypropionic herbicides such as chlorazifop, clofop, diclofop, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P and trifop; phenylenediamine herbicides such as dinitramine and prodiamine; pyrazolyl herbicides such as benzofenap, pyrazolynate, pyrazoxyfen, pyroxasulfone and topramezone; pyrazolylphenyl herbicides such as fluazolate and pyraflufen; pyridazine herbicides such as credazine, pyridafol and pyridate; pyridazinone herbicides such as brompyrazon, chloridazon, dimidazon, flufenpyr, metflurazon, oxapyrazon and pydanon; pyridine herbicides such as aminopyralid, cliodinate, clopyralid, dithiopyr, fluroxypyr, haloxydine, picloram and thiazopyr; pyrimidinediamine herbicides such as iprymidam and tioclorim; quaternary ammonium herbicides such as cyperquat, diethamquat, difenzoquat, diquat, morfamquat and paraquat; thiocarbamate herbicides such as butylate, cycloate, di-allate, EPTC, esprocarb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, pyributicarb, sulfallate, thiobencarb, tiocarbazil, tri-allate and vernolate; thiocarbonate herbicides such as dimexano, EXD and proxan; thiourea herbicides such as methiuron; triazine herbicides such as dipropetryn, triaziflam and trihydroxytriazine; chlorotriazine herbicides such as atrazine, chlorazine, cyanazine, cyprazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine, propazine, sebuthylazine, simazine, terbuthylazine and trietazine; methoxytriazine herbicides such as atraton, methometon, prometon, secbumeton, simeton and terbumeton; methylthiotriazine herbicides such as ametryn, aziprotryne, cyanatryn, desmetryn, dimethametryn, methoprotryne, prometryn, simetryn and terbutryn; triazinone herbicides such as ametridione, amibuzin, hexazinone, isomethiozin and metamitron; triazole herbicides such as amitrole, cafenstrole, epronaz and flupoxam; triazolone herbicides such as amicarbazone, bencarbazone, sulfentrazone and thiencarbazone-methyl; triazolopyrimidine herbicides such as cloransulam, diclosulam, flumetsulam and metosulam; uracil herbicides such as butafenacil, bromacil, flupropacil, isocil, lenacil and terbacil; 3-phenyluracils; urea herbicides such as benzthiazuron, cumyluron, cycluron, dichloralurea, isonoruron, isouron, methabenzthiazuron, monisouron and noruron; phenylurea herbicides such as anisuron, buturon, chlorbromuron, chloreturon, chloroxuron, daimuron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, linuron, methiuron, methyldymron, metobenzuron, metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tetrafluron and thidiazuron; pyrimidinylsulfonylurea herbicides such as azimsulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, foramsulfuron, imazosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, rimsulfuron, sulfometuron and trifloxysulfuron; triazinylsulfonylurea herbicides such as cinosulfuron, ethametsulfuron, metsulfuron, prosulfuron, triasulfuron, triflusulfuron and tritosulfuron; thiadiazolylurea herbicides such as buthiuron, ethidimuron, tebuthiuron, thiazafluron and thidiazuron; and unclassified herbicides such as acrolein, allyl alcohol, azafenidin, benazolin, benzobicyclon, buthidazole, calcium cyanamide, cambendichlor, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cinmethylin, CPMF, cresol, ortho-dichlorobenzene, dimepiperate, endothal, fluoromidine, fluridone, flurochloridone, flurtamone, fluthiacet, indanofan, methazole, methyl isothiocyanate, nipyraclofen, OCH, oxadiargyl, oxadiazon, oxaziclomefone, pentachlorophenol, pentoxazone, phenylmercury acetate, prosulfalin, pyribenzoxim, pyriftalid, quinoclamine, rhodethanil, sulglycapin, thidiazimin, tridiphane, trimeturon, tripropindan and tritac.

The synergistic composition of the present invention can, further, be used in conjunction with glyphosate, glufosinate, dicamba, imidazolinones or 2,4-D on glyphosate-tolerant, glufosinate-tolerant, dicamba-tolerant, imidazolinone-tolerant or 2,4-D-tolerant crops. It is generally preferred to use the synergistic composition of the present invention in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. It is further generally preferred to apply the synergistic composition of the present invention and other complementary herbicides at the same time, either as a combination formulation or as a tank mix.

The synergistic composition of the present invention can generally be employed in combination with known herbicide safeners, such as benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. Cloquintocet (mexyl) is a particularly preferred safener for the synergistic compositions of the present invention, specifically antagonizing any harmful effect of the synergistic compositions on rice and cereals.

In practice, it is preferable to use the synergistic composition of the present invention in mixtures containing an herbicidally effective amount of the herbicidal components along with at least one agriculturally acceptable adjuvant or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions.

Suitable agricultural adjuvants and carriers that are useful in preparing the herbicidal mixtures of the invention are well known to those skilled in the art.

Liquid carriers that can be employed include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is generally the carrier of choice for the dilution of concentrates.

Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.

It is usually desirable to incorporate one or more surface-active agents into the compositions of the present invention. Such surface-active agents are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surface-active agents include salts of alkyl sulfates, such as diethanol-ammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecyl-benzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C₁₈ ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C₁₆ ethoxylate; soaps, such as sodium stearate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethyl-ammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly used in agricultural compositions include compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.

The concentration of the active ingredients in the synergistic composition of the present invention is generally from 0.001 to 98 percent by weight. Concentrations from 0.01 to 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredients are generally present in a concentration from 5 to 98 weight percent, preferably 10 to 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds generally contain 0.0001 to 1 weight percent active ingredient and preferably contain 0.001 to 0.05 weight percent.

The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.

The following examples illustrate the present invention.

EXAMPLES Evaluation of Postemergence Herbicidal Activity of Mixtures in Cereal Crops

Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm²). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-36 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at about 18° C. during the day and 17° C. during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.

Treatments consisted of compound (as listed in Tables 1 through 64) and a second cereal herbicide alone and in combination. Weighed amounts of esters (methyl) or salts (TEA [triethylammonium], K [potassium]) of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (Compound A) or of 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid (Compound B), were placed in 25 milliliter (mL) glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 4.5 milligrams (mg) active ingredient (ai)/mL stock solutions. If the experimental compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions were diluted to 1.5 mg ai/mL with the addition of 2 volumes of an aqueous mixture containing acetone, water, isopropyl alcohol, DMSO, Agri-dex crop oil concentrate, and Triton® X-77 surfactant in a 64.7:26.0:6.7:2.0:0.7:0.01 v/v ratio. A dilution solution was prepared by mixing 1 volume of 97:3 v/v acetone/DMSO and 2 volumes of an aqueous mixture containing acetone, water, isopropyl alcohol, DMSO, Agri-dex crop oil concentrate, and Triton® X-77 surfactant in a 64.7:26.0:6.7:2.0:0.7:0.01 v/v ratio. Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha). Spray solutions of the second cereal herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingredients in two- and three-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m²) at a spray height of 18 inches (43 cm) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.

The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 days, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S. R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.).

The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration as used in the mixture.

B=observed efficacy of active ingredient B at the same concentration as used in the mixture.

Some of the compounds tested, application rates employed, plant species tested, and results are given in Table 1 through Table 64.

TABLE 1 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g /ha) Compound A ALOMY APESV AVEFA LOLMG SETVI Methyl Diflufenican Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 17.5 0  0 — 20 — 30 — 20 — 70 — 35 0 20 — 20 — 30 — 40 — 75 — 70 0 50 — 30 — 35 —  0 — 80 — 0 15  0 —  0 —  0 —  0 —  0 — 17.5 15 30  0 30 20 30 30 40 20 80 70 35 15 40 20 20 20 35 30 55 40 85 75 70 15 55 50 50 30 55 35 65 60 90 80

TABLE 2 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g/ha) Compound ALOMY LOLMG A Methyl Liberator* Ob Ex Ob Ex 17.5 0 0 — 20 — 35 0 20 — 40 — 70 0 50 — 60 — 0 75 0 — 0 — 17.5 75 30  0 40 20 35 75 30 20 45 40 70 75 45 50 50 60 *Liberator contains 100 g ai/l diflufenican and 400 g ai/l flufenacet

TABLE 3 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g /ha) Compound A Cloquintocet- ALOMY APESV AVEFA PHAMI Methyl Pinoxaden mexyl Ob Ex Ob Ex Ob Ex Ob Ex 35 0 0 30 — 10 — 40 — 30 — 70 0 0 30 — 10 — 45 — 35 — 0 7.5 1.875 53 — 70 — 30 — 25 — 0 15 3.75 93 — 93 — 93 — 85 — 35 7.5 1.875 85 67 90 73 80 58 85 48 70 7.5 1.875 90 67 80 73 85 62 85 51 35 15 3.75 100 95 90 93 100 96 90 90 70 15 3.75 95 95 85 93 100 96 90 90

TABLE 4 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g /ha) Compound A Clodinafop- Cloquintocet- ALOMY APESV AVEFA PHAMI Methyl propargyl mexyl Ob Ex Ob Ex Ob Ex Ob Ex 17.5 0 0 0 — 0 — 0 — 20 — 35 0 0 30 — 10 — 40 — 30 — 70 0 0 30 — 10 — 45 — 35 — 0 7 1.75 30 — 20 — 15 — 13 — 0 14 3.5 80 — 33 — 78 — 40 — 17.5 7 1.75 95 30 90 20 90 15 80 30 35 7 1.75 80 51 30 28 70 49 65 39 70 7 1.75 85 51 30 28 75 53 60 43 17.5 14 3.5 95 80 90 33 99 78 85 52 35 14 3.5 90 86 30 39 90 87 75 58 70 14 3.5 85 86 30 39 90 88 75 61

TABLE 5 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g /ha) Compound Mefenpyr- ALOMY APESV AVEFA PHAMI A Methyl Fenoxapropp diethyl Ob Ex Ob Ex Ob Ex Ob Ex 17.5 0 0 0 — 0 — 0 — 20 — 35 0 0 30 — 10 — 40 — 30 — 70 0 0 30 — 10 — 45 — 35 — 0 11.5 3.13 25 — 15 — 10 — 5 — 0 23 6.27 68 — 73 — 35 — 58 — 17.5 11.5 3.13 80 25 95 15 90 10 80 24 35 11.5 3.13 90 48 80 24 85 46 40 34 70 11.5 3.13 75 48 85 24 90 51 45 38 17.5 23 6.27 85 68 95 73 95 35 95 66 35 23 6.27 95 77 95 75 90 61 90 70 70 23 6.27 85 77 95 75 95 64 95 72

TABLE 6 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g/ha) Compound ALOMY PHAMI A Methyl Tralkoxydim Ob Ex Ob Ex 17.5 0 0 — 20 — 35 0 30 — 30 — 70 0 30 — 35 — 0 25 78 — 35 — 0 50 70 — 45 — 17.5 25 90 78 20 48 35 25 90 84 65 55 70 25 80 84 65 58 17.5 50 85 70 40 56 35 50 100 79 65 62 70 50 95 79 65 64

TABLE 7 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g/ha) Compound ALOMY SETVI A Methyl Iodosulfuron Ob Ex Ob Ex 35 0 3 — 77 — 70 0 20 — 82 — 140 0 47 — 91 — 0 2.5 50 — 0 — 35 2.5 83 52 70 77 70 2.5 73 60 89 82 140 2.5 80 73 97 91

TABLE 8 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g /ha) Compound BROTE A Methyl Mesosulfuron Ob Ex 35 0.0 0.0 — 70 0.0 0.0 — 140 0.0 13 — 0 3.8 73 — 35 3.8 73 73 70 3.8 77 73 140 3.8 82 77

TABLE 9 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g/ha) Compound BROTE POAAN A Methyl Atlantis WG* Ob Ex Ob Ex 35 0 0 — 0 — 70 0 0 — 3 — 140 0 13 — 3 — 0 4 67 — 50 — 35 4 75 67 57 50 70 4 77 67 53 52 140 4 80 71 53 52 *Atlantis WG contains 30 g/kg mesosulfuron and 6 g/kg iodosulfuron and 90 g/kg mefenpyr-diethyl

TABLE 10 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g /ha) Compound Propoxycarbazone- BROTE LOLMU POAAN A Methyl Na Ob Ex Ob Ex Ob Ex 35 0 0 — 3 — 0 — 70 0 0 — 20 — 3 — 140 0 13 — 40 — 3 — 0 25 92 — 17 — 7 — 35 25 95 92 50 19 37 7 70 25 96 92 53 33 37 10 140 25 94 93 53 50 37 10

TABLE 11 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g/ha) Compound PHAMI A Methyl Pyroxsulam* Ob Ex 35 0.0 3 — 70 0.0 6 — 140 0.0 17 — 0 3.8 78 — 35 3.8 84 79 70 3.8 89 80 140 3.8 92 82 *Pyroxsulam contains 30 g ai/l pyroxsulam and 90 g ai/l cloquintocet-mexyl

TABLE 12 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g/ha) Compound LOLRI A TEA Flupyrsulfuron Ob Ex 35 0 0 — 70 0 0 — 140 0 10 — 0 5 0 — 35 5 15 0 70 5 10 0 140 5 10 10

TABLE 13 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g /ha) Compound A LOLMG LOLRI LOLMU PHAMI TEA Imazamethabenz Ob Ex Ex Ex Ex 35 0 0 — 0 — 0 — 0 — 70 0 0 — 0 — 0 — 0 — 140 0 0 — 10 — 0 — 0 — 0 125 0 — 0 — 0 — 0 — 35 125 10 0 10 0 10 0 20 0 70 125 10 0 10 0 10 0 10 0 140 125 10 0 10 10 10 0 0 0

TABLE 14 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g /ha) Compound A ALOMY APESV AVEFA LOLMU TEA Iodosulfuron Ob Ex Ob Ex Ob Ex Ob Ex 35 0 0 — 8 — 0 — 0 — 70 0 0 — 13 — 0 — 3 — 140 0 3 — 15 — 0 — 3 — 0 2.5 50 — 68 — 35 — 53 — 35 2.5 53 50 91 70 60 35 65 53 70 2.5 60 50 87 72 50 35 74 54 140 2.5 70 51 94 73 64 35 59 54

TABLE 15 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g/ha) Compound APESV BROTE A TEA Mesosulfuron Ob Ex Ob Ex 35 0 3 — 0 — 70 0 0 — 0 — 140 0 4 — 0 — 0 3.75 93 — 75 — 35 3.75 96 93 78 75 70 3.75 95 93 78 75 140 3.75 96 93 76 75

TABLE 16 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g /ha) Compound A ALOMY APESV BROTE PHAMI POAAN TEA Atlantis WG* Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 35 0 0 — 3 — 0 — 0 — 0 — 70 0 0 — 0 — 0 — 0 — 0 — 140 0 0 — 4 — 0 — 0 — 0 — 0 3.6 95 — 96 — 73 — 97 — 63 — 35 3.6 96 95 98 96 75 73 99 97 64 63 70 3.6 95 95 97 96 75 73 99 97 65 63 140 3.6 97 95 98 96 78 73 99 97 69 63 *Atlantis WG contains 30 g/kg mesosulfuron and 6 g/kg iodosulfuron and 90 g/kg mefenpyr-diethyl

TABLE 17 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g /ha) Compound A Propoxycarbazone- APESV AVEFA LOLRI LOLMU POAAN TEA sodium Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 35 0 3 — 0 — 0 — 0 — 0 — 70 0 0 — 3 — 0 — 0 — 0 — 140 0 4 — 8 — 10 — 5 — 0 — 0 25 90 — 76 — 10 — 15 — 5 — 35 25 93 90 76 76 10 10 24 15 8 5 70 25 92 90 81 76 25 10 30 15 8 5 140 25 92 90 87 77 30 19 29 19 8 5

TABLE 18 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g /ha) Compound A ALOMY APESV AVEFA BROTE PHAMI TEA Pyroxsulam* Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 35 0 0 — 8 — 0 — 0 — 0 — 70 0 0 — 13 — 0 — 3 — 0 — 140 0 3 — 15 — 0 — 3 — 0 — 0 3.75 89 — 96 — 91 — 85 — 76 — 35 3.75 95 89 99 97 93 91 88 85 90 76 70 3.75 96 89 99 97 92 91 88 85 91 76 140 3.75 95 89 99 97 92 91 88 85 91 76 *Pyroxsulam contains 30 g ai/l pyroxsulam and 90 g ai/l cloquintocet-mexyl

TABLE 19 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application rate (g/ha) Compound ALOMY LOLRI A TEA Sulfosulfuron Ob Ex Ex 35 0 0 — 0 — 70 0 0 — 0 — 140 0 0 — 10 — 0 8.75 85 — 10 — 35 8.75 95 85 30 10 70 8.75 90 85 20 10 140 8.75 85 85 10 19

TABLE 20 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g /ha) Compound Cloquintocet- ALOMY APESV AVEFA PHAMI B Methyl Pinoxaden mexyl Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 0 0 — 0 — 0 — 0 — 17.5 0 0 10 — 0 — 0 — 0 — 35 0 0 20 — 0 — 0 — 0 — 70 0 0 40 — 0 — 0 — 0 — 0 15 3.75 80 — 85 — 90 — 85 — 8.75 15 3.75 90 80 90 85 100 90 95 85 17.5 15 3.75 90 82 90 85 95 90 95 85 35 15 3.75 95 84 90 85 95 90 95 85 70 15 3.75 90 88 90 85 95 90 95 85

TABLE 21 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g/ha) Compound Fenoxaprop- Mefenpyr- ALOMY APESV AVEFA LOLMG PESGL PHAMI B Methyl p ethyl diethyl Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 0 0 — 0 — 0 — 0 — 60 — 0 — 17.5 0 0 10 — 0 — 0 — 0 — 65 — 0 — 35 0 0 20 — 0 — 0 — 0 — 65 — 0 — 70 0 0 40 — 0 — 0 — 0 — 70 — 0 — 0 23 6.27 50 — 70 — 0 — 0 — 85 — 0 — 8.75 23 6.27 90 50 90 70 95 0 75 0 100 94 70 0 17.5 23 6.27 90 55 90 70 95 0 70 0 100 95 70 0 35 23 6.27 90 60 90 70 95 0 70 0 100 95 70 0 70 23 6.27 90 70 90 70 95 0 60 0 100 96 60 0

TABLE 22 Synergistic Activity of Herbicidal Compositions on Several Key Grass Weeds in Cereal Crops Application Rate (g/ha) Compound B ALOMY APESV LOLMG PHAMI Methyl Tralkoxydim Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 0 — 0 — 0 — 0 — 17.5 0 10 — 0 — 0 — 0 — 35 0 20 — 0 — 0 — 0 — 70 0 40 — 0 — 0 — 0 — 0 50 70 — 75 — 50 — 30 — 8.75 50 85 70 85 75 55 50 65 30 17.5 50 85 73 85 75 55 50 65 30 35 50 85 76 85 75 60 50 65 30 70 50 70 82 75 75 65 50 50 30

TABLE 23 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A CHEAL MATCH SINAR STEME VERPE VIOTR Methyl Diflufenican Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 17.5 0 90 — 15 — 70 — 78 — 45 — 55 — 35 0 90 — 68 — 80 — 90 — 58 — 63 — 70 0 95 — 65 — 85 — 100 — 70 — 75 — 0 15 0 — 5 — 0 — 3 — 38 15 — 17.5 15 100 90 65 19 85 70 88 78 78 67 78 62 35 15 100 90 80 69 90 80 100 90 80 73 85 68 70 15 100 95 80 67 100 85 100 100 93 81 90 79

TABLE 24 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A CHEAL MATCH SINAR STEME VERPE VIOTR Methyl Liberator* Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 17.5 0 90 — 20 — 80 — 75 — 40 — 40 — 35 0 90 — 85 — 85 — 95 — 55 — 50 — 70 0 95 — 80 — 85 — 100 — 80 — 60 — 0 75 30 — 10 — 30 — 20 — 10 — 10 — 17.5 75 100 93 70 28 85 86 100 80 65 46 70 46 35 75 100 93 95 87 85 90 100 96 75 60 75 55 70 75 100 97 95 82 95 90 100 100 90 82 85 64 *Liberator contains 100 g ai/l diflufenican and 400 g ai/l flufenacet

TABLE 25 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound BRSNN POLPE A Methyl Pyroxsulam* Ob Ex Ob Ex 8.75 0 50 — 50 — 17.5 0 50 — 50 — 35 0 50 — 65 — 70 0 50 — 70 — 0 7.5 75 — 75 — 8.75 7.5 100 88 95 88 17.5 7.5 100 88 95 88 35 7.5 100 88 95 91 70 7.5 100 88 95 93 *Pyroxsulam contains 30 g ai/l pyroxsulam and 90 g ai/l cloquintocet-mexyl

TABLE 26 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A VERHE KCHSC SINAR VIOTR VERPE TEA Picolinafen Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 10 — 35 — 35 — 10 — 10 — 17.5 0 20 — 60 — 60 — 10 — 10 — 35 0 50 — 65 — 65 — 30 — 30 — 70 0 75 — 70 — 70 — 60 — 60 — 0 12.5 5 — 5 — 5 — 0 — 0 — 8.75 12.5 30 15 60 38 95 38 10 10 10 10 17.5 12.5 80 24 65 62 95 62 20 10 30 10 35 12.5 65 53 75 67 75 67 60 30 60 30 70 12.5 85 76 85 72 85 72 75 60 75 60

TABLE 27 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A CIRAR VERPE VIOTR TEA Amidosulfuron Ob Ex Ob Ex Ob Ex 35 0 50 — 75 — 50 — 70 0 60 — 80 — 60 — 140 0 65 — 85 — 60 — 0 10 20 — 5 — 5 — 35 10 75 60 85 76 50 53 70 10 85 68 85 81 70 62 140 10 90 72 87 86 70 62

TABLE 28 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound VERPE A TEA Chlorsulfuron Ob Ex 35 0 75 — 70 0 80 — 140 0 85 — 0 2.2 5 — 35 2.2 87 76 70 2.2 95 81 140 2.2 95 86

TABLE 29 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A CIRAR VERPE VIOTR TEA Florasulam Ob Ex Ob Ex Ob Ex 35 0 50 — 75 — 50 — 70 0 60 — 80 — 60 — 140 0 65 — 85 — 60 — 0 1.25 20 — 5 — 10 — 35 1.25 90 60 95 76 70 55 70 1.25 95 68 95 81 65 64 140 1.25 95 72 97 86 70 64

TABLE 30 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) VERPE CIRAR VERPE VIOTR Compound A TEA Flupyrsulfuron Ob Ex Ob Ex Ob Ex Ob Ex 35 0 60 — 50 — 75 — 50 — 70 0 60 — 60 — 80 — 60 — 140 0 60 — 65 — 85 — 60 — 0 5 0 — 20 — 0 — 0 — 35 5 70 60 80 60 80 75 50 50 70 5 75 60 90 68 97 80 65 60 140 5 75 60 85 72 90 85 65 60

TABLE 31 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound CIRAR A TEA Iodosulfuron Ob Ex 35 0 50 — 70 0 60 — 140 0 65 — 0 3.75 50 — 35 3.75 90 75 70 3.75 93 80 140 3.75 95 83

TABLE 32 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A VERPE CIRAR VIOTR STEME MATCH TEA Mesosulfuron Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 35 0 60 — 50 — 50 — 55 — 60 — 70 0 60 — 60 — 60 — 60 — 60 — 140 0 60 — 65 — 60 — 65 — 65 — 0 3.75 0 — 20 — 0 — 0 — 5 — 35 3.75 75 60 95 60 65 50 70 55 60 62 70 3.75 75 60 95 68 65 60 70 60 80 62 140 3.75 75 60 95 72 70 60 75 65 85 67

TABLE 33 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound CIRAR A TEA Metsulfuron Ob Ex 35 0 50 — 70 0 60 — 140 0 65 — 0 3.75 20 — 35 3.75 80 60 70 3.75 85 68 140 3.75 85 72

TABLE 34 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound Propoxycarbazone- VERPE MATCH A TEA sodium Ob Ex Ob Ex 35 0 75 — 60 — 70 0 80 — 60 — 140 0 85 — 65 — 0 15 5 — 50 — 35 15 75 76 80 80 70 15 90 81 87 80 140 15 95 86 87 83

TABLE 35 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound CIRAR A TEA Pyroxsulam* Ob Ex 35 0 50 — 70 0 60 — 140 0 65 — 0 3.75 20 — 35 3.75 90 60 70 3.75 95 68 140 3.75 95 72 *Pyroxsulam contains 30 g ai/l pyroxsulam and 90 g ai/l cloquintocet-mexyl

TABLE 36 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound CIRAR VERPE A TEA Sulfosulfuron Ob Ex Ob Ex 35 0 50 — 75 — 70 0 60 — 80 — 140 0 65 — 85 — 0 8.75 10 — 30 — 35 8.75 75 55 80 83 70 8.75 93 64 97 86 140 8.75 80 69 97 90

TABLE 37 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound CIRAR A TEA Thifensulfuron Ob Ex 35 0 50 — 70 0 60 — 140 0 65 — 0 3.75 20 — 35 3.75 80 60 70 3.75 90 68 140 3.75 85 72

TABLE 38 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound CIRAR A TEA Tribenuron Ob Ex 35 0 50 — 70 0 60 — 140 0 65 — 0 3.75 20 — 35 3.75 93 60 70 3.75 95 68 140 3.75 95 72

TABLE 39 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound STEME MATCH A TEA Imazamethabenz Ob Ex Ob Ex 35 0 55 — 60 — 70 0 60 — 60 — 140 0 65 — 65 — 0 125 10 — 0 — 35 125 75 60 60 60 70 125 100 64 80 60 140 125 100 69 80 65

TABLE 40 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A BRSNI GERDI POLCO STEME VERPE VIOTR TEA Beflubutamid Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 70 — 50 — 90 — 80 — 48 — 30 — 17.5 0 91 — 55 — 93 — 85 — 68 — 40 — 35 0 98 — 65 — 98 — 88 — 79 — 47 — 0 35 30 — 0 — 10 — 10 — 15 — 15 — 0 70 30 — 0 — 20 — 10 — 23 — 23 — 8.75 35 85 79 60 50 100 91 95 82 61 56 68 41 17.5 35 100 94 60 55 100 93 100 87 79 73 66 49 35 35 100 98 75 65 100 98 100 89 84 82 76 55 8.75 70 100 79 70 50 100 92 100 82 61 60 49 46 17.5 70 100 94 75 55 100 94 100 87 83 76 74 54 35 70 100 98 80 65 100 98 100 89 89 84 80 59

TABLE 41 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) BRSNI POLCO VERPE VIOTR Compound A TEA Bentazone Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 70 — 90 — 48 — 30 — 17.5 0 91 — 93 — 68 — 40 — 35 0 98 — 98 — 79 — 47 — 70 0 99 — 99 — 88 — 60 — 0 120 50 — 0 — 0 — 0 — 8.75 120 100 85 100 90 65 48 60 30 17.5 120 100 96 97 93 70 68 65 40 35 120 100 99 100 98 87 79 70 47 70 120 100 99 100 99 93 88 75 60

TABLE 42 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) BRSNI MATCH STEME Compound A TEA Bromoxynil Ob Ex Ob Ex Ob Ex 8.75 0 70 — 71 — 80 — 17.5 0 91 — 76 — 85 — 35 0 98 — 84 — 88 — 70 0 99 — 94 — 93 — 0 70 50 — 0 — 0 — 17.5 70 100 96 85 76 97 85 35 70 100 99 93 84 97 88 70 70 100 99 95 94 100 93

TABLE 43 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A BRSNI GERDI KCHSC MATCH POLCO STEME TEA Chlormequat Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 70 — 50 — 65 — 71 — 90 — 80 — 17.5 0 91 — 55 — 77 — 76 — 93 — 85 — 35 0 98 — 65 — 92 — 84 — 98 — 88 — 70 0 99 — 78 — 99 — 94 — 99 — 93 — 0 155 0 — 0 — 0 — 0 — 10 — 0 — 8.75 155 100 70 75 50 70 65 93 71 100 91 100 80 17.5 155 100 91 75 55 100 77 100 76 100 93 100 85 35 155 100 98 60 65 100 92 100 84 100 98 100 88 70 155 100 99 50 78 100 99 100 94 100 99 100 93

TABLE 44 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound BRSNI KCHSC A TEA Chlorotoluron Ob Ex Ob Ex 8.75 0 70 — 65 — 17.5 0 91 — 77 — 35 0 98 — 92 — 70 0 99 — 99 — 0 450 50 — 50 — 8.75 450 100 85 100 83 17.5 450 100 96 100 89 35 450 100 99 97 96

TABLE 45 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) MATCH POLCO STEME Compound A TEA Indol-3-acetic acid Ob Ex Ob Ex Ob Ex 8.75 0 71 — 90 — 80 — 17.5 0 76 — 93 — 85 — 35 0 84 — 98 — 88 — 70 0 94 — 99 — 93 — 0 140 0 — 0 — 0 — 8.75 140 80 71 100 90 85 80 17.5 140 90 76 100 93 97 85 35 140 93 84 100 98 100 88 70 140 95 94 100 99 100 93

TABLE 46 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound Indol-3-butyric BRSNI STEME A TEA acid Ob Ex Ob Ex 8.75 0 70 — 80 — 17.5 0 91 — 85 — 35 0 98 — 88 — 70 0 99 — 93 — 0 140 0 — 0 — 8.75 140 80 70 80 80 17.5 140 93 91 90 85 35 140 100 98 100 88 70 140 100 99 100 93

TABLE 47 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) BRSNI KCHSC SASKR VIOTR Compound A TEA Isoproturon Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 70 — 65 — 80 — 30 — 17.5 0 91 — 77 — 84 — 40 — 35 0 98 — 92 — 87 — 47 — 70 0 99 — 99 — 93 — 60 — 0 300 40 — 50 — 33 — 0 — 8.75 300 93 82 100 83 89 87 30 30 17.5 300 100 95 100 89 90 89 45 40 35 300 100 99 100 96 97 91 60 47 70 300 100 99 97 99 95 95 73 60

TABLE 48 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound VERPE VIOTR A TEA Isoxaben Ob Ex Ob Ex 8.75 0 48 — 30 — 17.5 0 68 — 40 — 35 0 79 — 47 — 70 0 88 — 60 — 0 31.25 0 — 3 — 8.75 31.25 61 48 48 32 17.5 31.25 71 68 50 42 35 31.25 84 79 61 48 70 31.25 95 88 70 61

TABLE 49 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound BRSNI VERPE VIOTR A TEA Metribuzin Ob Ex Ob Ex Ob Ex 8.75 0  70 — 48 — 30 — 17.5 0  91 — 68 — 40 — 35 0  98 — 79 — 47 — 70 0  99 — 88 — 60 — 0 50  50 — 10 — 20 — 8.75 50 100 85 60 53 60 44 17.5 50 100 96 90 72 80 52 35 50 100 99 90 81 80 58 70 50 100 99 95 89 85 68

TABLE 50 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) BRSNI MATCH SASKR STEME Compound A TEA Prosulfocarb Ob Ex Ob Ex Ob Ex Ob Ex 8.75  0  70 — 71 — 80 —  80 — 17.5  0  91 — 76 — 84 —  85 — 35  0  98 — 84 — 87 —  88 — 70  0  99 — 94 — 93 —  93 — 0 500   0 —  0 —  0 —   0 — 8.75 500  97 70 95 71 85 80  85 80 17.5 500 100 91 95 76 90 84  85 85 35 500 100 98 97 84 90 87 100 88 70 500 100 99 95 94 90 93 100 93

TABLE 51 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound KCHSC STEME A TEA Quinclorac Ob Ex Ob Ex 8.75 0 65 — 80 — 17.5 0 77 — 85 — 35 0 92 — 88 — 70 0 99 — 93 — 0 140 0 — 0 — 8.75 140 65 65 87 80 17.5 140 90 77 90 85 35 140 100 92 100 88 70 140 100 99 100 93

TABLE 52 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) GERDI MATCH BRSNI Compound A TEA Aminopyralid Ob Ex Ob Ex Ob Ex 8.75 0 38 — 59 —  83 — 17.5 0 50 — 76 —  93 — 35 0 80 — 88 —  97 — 70 0 85 — 93 — 100 — 0 2.5  0 — 10 —  0 — 8.75 2.5 65 38 90 63  93 83 17.5 2.5 60 50 95 78  97 93

TABLE 53 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) MATCH VERPE BRSNI Compound A TEA Dicamba Ob Ex Ob Ex Ob Ex 8.75 0 59 — 59 —  83 — 17.5 0 76 — 69 —  93 — 35 0 88 — 86 —  97 — 70 0 93 — 85 — 100 — 0 35 30 — 10 —  50 — 8.75 35 87 71 80 63  95 92 17.5 35 90 83 85 72 100 97

TABLE 54 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound MATCH VERPE A TEA Dichlorprop Ob Ex Ob Ex 8.75 0 59 — 59 — 17.5 0 76 — 69 — 35 0 88 — 86 — 70 0 93 — 85 — 0 140 10 — 20 — 8.75 140 87 63 80 67 17.5 140 90 78 85 75

TABLE 55 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound POLCO VERPE VIOTR STEME POLPE A TEA MCPA Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0  76 — 59 — 34 — 76 — 30 — 17.5 0  88 — 69 — 44 — 85 — 41 — 35 0  96 — 86 — 58 — 91 — 68 — 0 70   7 — 10 — 17 —  7 — 23 — 8.75 70  83 78 73 63 53 45 89 78 45 46 17.5 70  95 88 80 72 60 53 94 86 65 55 35 70 100 96 87 87 72 65 98 92 84 75

TABLE 56 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound BRSNN MATCH B Methyl Pyroxsulam* Ob Ex Ob Ex 8.75 0 20 — 10 — 17.5 0 35 — 10 — 35 0 50 — 40 — 70 0 55 — 45 — 0 3.75 90 — 65 — 8.75 3.75 99 92 90 69 17.5 3.75 99 94 85 69 35 3.75 99 95 85 79 70 3.75 100 96 85 81 *Pyroxsulam contains 30 g ai/l pyroxsulam and 90 g ai/l cloquintocet-mexyl

TABLE 57 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound A Amino- MATCH SASKR KCHSC VERPE VIOTR K-salt pyralid Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 50 — 63 — 67 — 73 — 20 — 17.5 0 62 — 67 — 77 — 78 — 48 — 35 0 57 — 73 — 90 — 83 — 42 — 0 2.5  8 — 18 —  0 —  0 — 27 — 8.75 2.5 72 54 75 70 75 67 82 73 57 41 17.5 2.5 80 65 85 73 88 77 87 78 70 62 35 2.5 85 60 90 78 95 90 85 83 72 57

TABLE 58 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) MATCH SASKR VERPE VIOTR Compound A K-salt Picolinafen Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 50 — 63 — 73 — 20 — 17.5 0 62 — 67 — 78 — 48 — 35 0 57 — 73 — 83 — 42 — 0 15 10 — 60 — 43 — 78 — 8.75 15 90 55 83 85 95 85 95 83 17.5 15 83 66 90 87 95 88 88 89 35 15 87 61 95 89 98 91 98 87

TABLE 59 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound Aminopyralid + MATCH VERPE VIOTR A K-salt Picolinafen Ob Ex Ob Ex Ob Ex 8.75 0 50 —  73 —  20 — 17.5 0 62 —  78 —  48 — 35 0 57 —  83 —  42 — 0 2.5 + 15 25 —  38 —  72 — 8.75 2.5 + 15 70 59  98 85 100 87 17.5 2.5 + 15 73 68 100 88  96 92 35 2.5 + 15 90 64  99 91 100 91

TABLE 60 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) MATCH KCHSC VERPE VIOTR Compound A K-salt Diflufenican Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 50 — 67 — 73 — 20 — 17.5 0 62 — 77 — 78 — 48 — 35 0 57 — 90 — 83 — 42 — 0 12.5  7 — 12 —  7 — 35 — 8.75 12.5 82 53 80 71 88 75 58 48 17.5 12.5 85 64 82 79 90 80 80 66 35 12.5 87 60 90 91 93 84 82 62

TABLE 61 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound Aminopyralid + MATCH KCHSC VERPE VIOTR A K-salt Diflufenican Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 50 — 67 — 73 — 20 — 17.5 0 62 — 77 — 78 — 48 — 35 0 57 — 90 — 83 — 42 — 0 2.5 + 12.5 23 — 27 — 35 — 63 — 8.75 2.5 + 12.5 80 57 82 71 95 75 86 62 17.5 2.5 + 12.5 80 67 85 79 93 80 90 75 35 2.5 + 12.5 83 63 93 91 93 84 93 72

TABLE 62 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound MATCH VERPE VIOTR A K-salt Florasulam Ob Ex Ob Ex Ob Ex 8.75 0 50 — 73 — 20 — 17.5 0 62 — 78 — 48 — 35 0 57 — 83 — 42 — 0 1.3 83 — 28 — 53 — 8.75 1.3 95 92 80 81 77 63 17.5 1.3 98 94 91 85 80 76 35 1.3 98 93 90 88 80 73

TABLE 63 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound SASKR KCHSC VIOTR A K-salt Glyphosate Ob Ex Ob Ex Ob Ex 8.75 0 63 — 67 — 20 — 17.5 0 67 — 77 — 48 — 35 0 73 — 90 — 42 — 0 52.5  0 —  0 — 52 — 8.75 52.5 83 63 68 67 75 61 17.5 52.5 87 67 83 77 77 75 35 52.5 87 73 87 90 83 72

TABLE 64 Synergistic Activity of Herbicidal Compositions on Several Key Broadleaf Weeds in Cereal Crops Application Rate (g/ha) Compound Pyrasulfotole + MATCH KCHSC VERPE VIOTR A K-salt Bromoxynil Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 50 —  67 — 73 — 17.5 0 62 —  77 — 78 — 35 0 57 —  90 — 83 — 0 25.6 23 —  58 — 30 — 8.75 25.6 73 62  90 86 88 81 17.5 25.6 70 71  93 90 90 85 35 25.6 78 67  92 96 92 88 0 51.3 37 —  78 — 30 — 83 — 8.75 51.3 80 68  97 93 87 81 93 87 17.5 51.3 84 76 100 95 95 85 95 91 35 51.3 87 73  98 98 98 88 88 90

-   ALOMY=Alopecurus myosuroides LOLMG=Lolium multiflorum -   APESV=Apera spica-venti SETVI=Setaria viridis -   AVEFA=Avena fatua CHEAL=Chenopodium album -   MATCH=Matricaria chamomila SINAR=Sinapis arvensis -   STEME=Stellaria media VERPE=Veronica persica -   VIOTR=Viola tricolor BRSNN=Brassica napus -   CIRAR=Cirsium arvense POLPE=Polygonum persicaria -   PHAMI=Phalaris minor VERHE=Veronica hederifolia -   KCHSC=Kochia scoparia BROTE=Bromus tectorum -   POAAN=Poa annua LOLMU=Lolium multiflorum -   LOLRI=Lolium rigidum PESGL=Pennisetum americanum -   BRSNI=Brassica nigra GERDI=Geranium dissectum -   POLCO=Polygonum convolvulus SASKR=Salsola iberica

Evaluation of Postemergence Herbicidal Mixtures for Weed Control in Direct Seeded Rice

Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam soil (43 percent silt, 19 percent clay, and 38 percent sand, with a pH of about 8.1 and an organic matter content of about 1.5 percent) and river sand in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a surface area of 139.7 cm². When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 10-17 days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29° C. during the day and 26° C. during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.

Treatments consisted of esters (methyl, n-butyl or allyl) or salts (TEA [triethylammonium]) of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (Compound A), 4-amino-3-chloro-6-(2,4-dichloro-3-methoxyphenyl)pyridine-2-carboxylic acid (Compound C), or 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-ethoxyphenyl)pyridine-2-carboxylic acid (Compound D), and various herbicidal components alone and in combination. Weighed amounts were placed in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12× stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions were added to the spray solutions so that the final acetone and DMSO concentrations were 16.2% and 0.5%, respectively. Spray solutions were diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) Agri-dex crop oil concentrate. The final spray solutions contained 1.25% (v/v) Agri-dex crop oil concentrate. Compound requirements are based upon a 12 mL application volume at a rate of 187 L/ha. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m² at a spray height of 18 inches (43 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.

Forms of compounds A, C, and D were applied on an acid equivalent basis. Other herbicidal components were applied on an active ingredient basis and included acetolactate synthase (ALS)-inhibiting herbicides penoxsulam (triazolopyrimidine chemical class) applied as Grasp SC, bispyribac-sodium (pyrimidinylbenzoate chemical class) applied as Regiment 80 DF, halosulfuron-methyl (sulfonylurea chemical class) applied as Permit, bensulfuron-methyl (sulfonylurea chemical class) applied as Londax, imazethapyr (imidazolinone chemical class) applied as Newpath, and imazamox (imidazolinone chemical class) applied as Beyond; EPSP synthase inhibiting herbicide glyphosate applied as Glyphomax; photosystem II (PSII)-inhibiting herbicide propanil applied as Stam 80 EDF; protoporphyrinogen IX oxidase (Protox)-inhibiting herbicide carfentrazone-ethyl applied as Aim EC; acetyl CoA carboxylase (ACCase) inhibiting herbicides cyhalofop-butyl applied as Clincher SF and fenoxaprop-p-ethyl applied as Ricestar HT; auxinic herbicides triclopyr applied as Grandstand, MCPA EHE, and quinclorac applied as Facet 75 DF; auxin transport inhibiting herbicide diflufenzopyr; phytoene desaturase inhibiting herbicide norflurazon, p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting herbicide sulcotrione applied as Mikado; other carotenoid biosynthesis inhibiting herbicides clomazone applied as Command 3 ME and pyriclor.

The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 3 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S. R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.).

The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration as used in the mixture.

B=observed efficacy of active ingredient B at the same concentration as used in the mixture.

Some of the herbicide combinations tested, application rates employed, plant species tested, and results are given in Tables 65-98.

TABLE 65 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound IPOHE Compound C IPOHE A Methyl Penoxsulam Ob Ex Methyl Penoxsulam Ob Ex 4.38 0 10 — 4.38 0 40 — 8.75 0 15 — 8.75 0 70 — 0 4.38 70 — 0 4.38 70 — 0 8.75 60 — 0 8.75 60 — 4.38 4.38 100 73 4.38 4.38 75 82 8.75 4.38 90 75 8.75 4.38 95 91 4.38 8.75 75 64 4.38 8.75 90 76 8.75 8.75 90 66 8.75 8.75 85 88

TABLE 66 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound LEFCH Compound LEFCH A Methyl Penoxsulam Ob Ex A n-Butyl Penoxsulam Ob Ex 8.75 0 40 — 8.75 0 10 — 0 17.5 0 — 17.5 0 30 — 0 35 0 — 0 35 0 — 8.75 17.5 80 40 8.75 35 20 10 8.75 35 75 40 17.5 35 60 30

TABLE 67 Synergistic Activity of Herbicidal Compositions on a Key Sedge Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A CYPES Compound A CYPES Methyl Penoxsulam Ob Ex n-Butyl Penoxsulam Ob Ex 4.38 0 70 — 8.75 0 50 — 8.75 0 30 — 17.5 0 85 — 0 17.5 10 — 0 17.5 10 — 4.38 17.5 95 73 8.75 17.5 90 55 8.75 17.5 95 37 17.5 17.5 99 87 Application Rate (g/ha) Compound C CYPES Methyl Penoxsulam Ob Ex 8.75 0 30 — 17.5 0 65 — 0 17.5 10 — 8.75 17.5 95 37 17.5 17.5 90 69

TABLE 68 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A Bispyribac- IPOHE Compound A Bispyribac- IPOHE Methyl sodium Ob Ex n-Butyl sodium Ob Ex 4.38 0 0 — 8.75 0 35 — 8.75 0 10 — 17.5 0 30 — 0 7 10 — 0 7 10 — 0 14 50 — 0 14 15 — 0 28 60 — 17.5 7 55 37 4.38 7 20 10 8.75 14 100 45 8.75 7 50 10 17.5 14 95 41 4.38 14 75 50 8.75 14 60 55 4.38 28 90 60 8.75 28 95 64 Application Rate (g/ha) Compound C Bispyribac- IPOHE Methyl sodium Ob Ex 8.75 0 30 — 17.5 0 50 — 0 7 10 — 0 14 15 — 8.75 7 45 37 17.5 7 80 55 8.75 14 50 41 17.5 14 90 58

TABLE 69 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A Bispyribac- CYPES CYPIR Compound C Bispyribac- CYPIR Methyl sodium Ob Ex Ob Ex Methyl sodium Ob Ex 4.38 0 85 — 70 — 8.75 0 25 — 8.75 0 90 — 70 — 17.5 0 40 — 0 14 0 — 90 — 0 7 40 — 0 28 50 — 95 — 0 14 90 — 4.38 14 90 85 95 97 8.75 7 99 55 8.75 14 100 90 99 97 17.5 7 95 64 4.38 28 95 93 100 99 8.75 14 100 93 8.75 28 100 95 95 99 17.5 14 100 94

TABLE 70 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A Halosulfuron- LEFCH Compound A Halosulfuron- LEFCH Methyl methyl Ob Ex n-Butyl methyl Ob Ex 8.75 0 40 — 17.5 0 30 — 0 26 0 — 35 0 60 — 0 52 0 — 0 26 0 — 8.75 26 50 40 0 52 0 — 8.75 52 60 40 17.5 26 45 30 35 26 95 60 17.5 52 40 30 35 52 85 60

TABLE 71 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A Bensulfuron- LEFCH Compound C Bensulfuron- LEFCH Methyl methyl Ob Ex Methyl methyl Ob Ex 4.38 0 30 — 4.38 0 0 — 0 4.38 20 — 0 4.38 20 — 0 8.75 0 — 0 8.75 0 — 4.38 4.38 55 44 4.38 4.38 45 20 4.38 8.75 99 30 4.38 8.75 55 0

TABLE 72 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A ISCRU Compound A ISCRU Methyl Imazethapyr Ob Ex n-Butyl Imazethapyr Ob Ex 8.75 0 50 — 35 0 20 — 17.5 0 55 — 70 0 50 — 0 35 20 — 0 35 20 — 8.75 35 90 60 35 35 70 36 17.5 35 90 64 70 35 95 60

TABLE 73 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A ISCRU Compound A ISCRU Methyl Imazamox Ob Ex n-Butyl Imazamox Ob Ex 8.75 0 50 — 35 0 20 — 17.5 0 55 — 70 0 50 — 0 22.4 50 — 0 22.4 50 — 8.75 22.4 80 75 35 22.4 85 60 17.5 22.4 95 78 70 22.4 100 75

TABLE 74 Synergistic Activity of Herbicidal Compositions on Key Broadleaf Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A IPOHE POLPE Compound C IPOHE POLPE Methyl Propanil Ob Ex Ob Ex Methyl Propanil Ob Ex Ob Ex 8.75 0 85 — 50 — 35 0 65 — 85 — 17.5 0 85 — 90 — 70 0 85 — 100 — 0 560 10 — 10 — 0 560 10 — 10 — 0 1120 10 — 40 — 0 1120 10 — 40 — 8.75 560 95 87 100 55 35 560 70 69 100 87 17.5 560 100 87 80 91 70 560 90 87 100 100 8.75 1120 100 87 100 70 35 1120 95 69 100 91 17.5 1120 95 87 70 94 70 1120 100 87 100 100

TABLE 75 Synergistic Speed of Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury at 11 DAA % Injury at 21 DAA Application Rate (g/ha) Application Rate (g/ha) Compound A CYPIR SCPMA Compound A CYPIR SCPMA n-Butyl Propanil Ob Ex Ob Ex n-Butyl Propanil Ob Ex Ob Ex 35 0 60 — 30 — 35 0 60 — 50 — 70 0 90 — 100 — 70 0 100 — 100 — 0 560 10 — 30 — 0 560 0 — 0 — 0 1120 10 — 30 — 0 1120 0 — 0 — 35 560 100 64 50 51 35 560 100 60 50 50 70 560 95 91 100 100 70 560 99 100 100 100 35 1120 90 64 90 51 35 1120 99 60 100 50 70 1120 100 91 95 100 70 1120 100 100 100 100

TABLE 76 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Compound Carfentrazone- POLPE A n-Butyl ethyl Ob Ex 4.38 0 40 — 8.75 0 60 — 0 14 0 — 4.38 14 50 40 8.75 14 100 60

TABLE 77 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A Carfentrazone- CYPES Compound A Carfentrazone- CYPIR Methyl ethyl Ob Ex n-Butyl ethyl Ob Ex 4.38 0 85 — 8.75 0 50 — 8.75 0 90 — 17.5 0 90 — 0 56 10 — 0 56 10 — 0 112 0 — 0 112 0 — 4.38 56 100 87 8.75 56 85 55 8.75 56 100 91 17.5 56 90 91 4.38 112 100 85 8.75 112 100 50 8.75 112 100 90 17.5 112 100 90 Application Rate (g/ha) Application Rate (g/ha) Compound C Carfentrazone- CYPES Compound C Carfentrazone- CYPIR Methyl ethyl Ob Ex Methyl ethyl Ob Ex 8.75 0 65 — 8.75 0 25 — 17.5 0 100 — 17.5 0 40 — 0 56 10 — 0 14 0 — 0 112 0 — 0 28 0 — 8.75 56 100 68 8.75 14 50 25 17.5 56 85 100 17.5 28 100 40 8.75 112 100 65 17.5 112 99 100

TABLE 78 Synergistic Speed of Activity of Herbicidal Compositions on a Key Sedge Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound Carfentrazone- 11 DAA CYPES 21 DAA CYPES A Methyl ethyl Ob Ex Ob Ex 8.75 0 60 — 100 — 17.5 0 70 — 99 — 0 14 10 — 0 — 0 28 10 — 0 — 8.75 14 100 64 95 100 17.5 14 100 73 99  99 8.75 28 100 64 100 100 17.5 28 70 73 80  99 % Injury Application Rate (g/ha) Compound Carfentrazone- 11 DAA CYPES 21 DAA CYPES A n-Butyl ethyl Ob Ex Ob Ex 35 0 50 — 90 — 70 0 75 — 100 — 0 14 10 — 0 — 0 28 10 — 0 — 35 14 70 55 85  90 70 14 80 78 99 100 35 28 100 55 100  90 70 28 100 78 100 100

TABLE 79 Synergistic Activity of Herbicidal Compositions on Key Broadleaf Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A Cyhalofop- IPOHE Compound C Cyhalofop- IPOHE Methyl butyl Ob Ex Methyl butyl Ob Ex 8.75 0 40 — 8.75 0 10 — 17.5 0 75 — 17.5 0 40 — 0 280 0 — 35 0 20 — 8.75 280 90 40 0 140 0 — 17.5 280 90 75 0 280 0 — 8.75 140 85 10 17.5 140 85 40 35 140 90 20 8.75 280 40 10 17.5 280 90 40 35 280 90 20 Application Rate (g/ha) Application Rate (g/ha) Compound A Cyhalofop- POLPY Compound A Cyhalofop- POLPY Methyl butyl Ob Ex n-Butyl butyl Ob Ex 4.38 0 50 — 8.75 0 40 — 8.75 0 60 — 17.5 0 90 — 0 100 0 — 0 100 0 — 4.38 100 0 — 8.75 100 0 — 8.75 100 40 50 17.5 100 55 40 0 200 50 60 0 200 95 90 4.38 200 65 50 8.75 200 80 40 8.75 200 75 60 17.5 200 95 90 Application Rate (g/ha) Compound C Cyhalofop- POLPY Methyl butyl Ob Ex 8.75 0 10 — 17.5 0 15 — 0 100 0 — 8.75 100 0 — 17.5 100 20 10 0 200 35 15 8.75 200 10 10 17.5 200 30 15

TABLE 80 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound C Cyhalofop- CYPES Compound A Cyhalofop- CYPIR Methyl butyl Ob Ex Methyl butyl Ob Ex 8.75 0 30 — 8.75 0 30 — 17.5 0 65 — 35 0 50 — 0 100 0 — 0 140 0 — 0 200 0 — 0 280 0 — 8.75 100 85 30 8.75 140 40 30 17.5 100 85 65 35 140 85 50 8.75 200 95 30 8.75 280 35 30 17.5 200 95 65 35 280 75 50 Application Rate (g/ha) Application Rate (g/ha) Compound C Cyhalofop- CYPIR Compound D Cyhalofop- CYPIR Methyl butyl Ob Ex Methyl butyl Ob Ex 17.5 0 0 — 8.75 0 50 — 35 0 40 — 35 0 80 — 0 140 0 — 0 140 0 — 0 280 0 — 0 280 0 — 17.5 140 25 0 8.75 140 60 50 35 140 80 40 35 140 75 80 17.5 280 50 0 8.75 280 70 50 35 280 70 40 35 280 95 80

TABLE 81 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound Fenoxaprop- POLPY A Allyl p-ethyl Ob Ex 17.5 0 70 — 0 35 0 — 17.5 35 85 70

TABLE 82 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Compound Fenoxaprop- FIMMI SCPMA A Allyl p-ethyl Ob Ex Ob Ex 17.5 0 40 — 0 — 0 35 0 — 0 — 17.5 35 95 40 40 0

TABLE 83 Synergistic Activity of Herbicidal Compositions on a Key Sedge Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound Triclopyr- CYPES C Methyl TEA Ob Ex 8.75 0 65 — 0 140 0 — 0 280 0 — 8.75 140 100 65 8.75 280 90 65

TABLE 84 Synergistic Activity of Herbicidal Compositions on Key Grass Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Compound MCPA BRAPP ISCRU A Allyl EHE Ob Ex Ob Ex 8.75 0 60 — 10 — 17.5 0 99 — 40 — 0 70 0 — 0 — 0 140 0 — 0 — 8.75 70 80 60 0 10 17.5 70 70 99 20 40 8.75 140 100 60 50 10 17.5 140 85 99 50 40

TABLE 85 Synergistic Activity of Herbicidal Compositions on a Key Sedge Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound MCPA FIMMI A Allyl EHE Ob Ex 8.75 0 0 — 17.5 0 20 — 0 70 0 — 0 140 0 — 8.75 70 40  0 17.5 70 30 20 8.75 140 80  0 17.5 140 95 20

TABLE 86 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A CYPIR Compound A FIMMI Methyl Quinclorac Ob Ex Allyl Quinclorac Ob Ex 4.38 0 30 — 8.75 0 0 — 8.75 0 75 — 17.5 0 40 — 0 140 0 — 0 140 0 — 4.38 140 70 30 8.75 140 60 0 8.75 140 85 75 17.5 140 100 40

TABLE 87 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound IPOHE A Methyl Diflufenzopyr Ob Ex 4.38 0 20 — 8.75 0 40 — 17.5 0 75 — 0 4.38 10 — 0 8.75 40 — 0 17.5 60 — 0 35 65 — 4.38 4.38 30 28 8.75 4.38 65 46 17.5 4.38 90 78 4.38 8.75 65 52 8.75 8.75 65 64 17.5 8.75 80 85 4.38 17.5 75 68 8.75 17.5 90 76 17.5 17.5 95 90 4.38 35 70 72 8.75 35 85 79 17.5 35 95 91

TABLE 88 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound LEFCH A Methyl Diflufenzopyr Ob Ex 4.38 0 30 — 8.75 0 80 — 17.5 0 75 — 35 0 90 — 0 8.75 0 — 4.38 8.75 45 30 8.75 8.75 90 80 17.5 8.75 95 75 35 8.75 90 90

TABLE 89 Synergistic Activity of Herbicidal Compositions on a Key Sedge Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound CYPIR A Methyl Diflufenzopyr Ob Ex 8.75 0 30 — 35 0 50 — 0 4.38 10 — 0 8.75 15 — 0 17.5 20 — 0 35 30 — 8.75 4.38 25 37 35 4.38 85 55 8.75 8.75 55 41 35 8.75 90 58 8.75 17.5 60 44 35 17.5 95 60 8.75 35 60 51 35 35 95 65

TABLE 90 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound LEFCH A Methyl Clomazone Ob Ex 4.38 0 10 — 17.5 0 50 — 0 560 40 — 4.38 560 85 46 17.5 560 99 70

TABLE 91 Synergistic Activity of Herbicidal Compositions on a Key Sedge Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound CYPIR A Methyl Clomazone Ob Ex 4.38 0 80 — 0 560 0 — 0 1120 0 — 4.38 560 90 80 4.38 1120 100 80

TABLE 92 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound A BRAPP Compound A BRAPP Methyl Norflurazon Ob Ex Allyl Norflurazon Ob Ex 8.75 0 60 — 8.75 0 80 — 0 70 0 — 0 70 0 — 8.75 70 90 60 8.75 70 95 80

TABLE 93 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Compound A CYPES CYPIR FIMMI SCPMA Methyl Norflurazon Ob Ex Ob Ex Ob Ex Ob Ex 4.38 0 40 — 25 — 20 — 0 — 8.75 0 60 — 50 — 40 — 10 — 0 560 0 — 0 — 0 — 60 — 4.38 560 90 40 20 25 65 20 80 60 8.75 560 99 60 90 50 90 40 90 64 Application Rate (g/ha) Compound A CYPES CYPIR FIMMI SCPMA Allyl Norflurazon Ob Ex Ob Ex Ob Ex Ob Ex 17.5 0 50 — 35 — 50 — 10 — 35 0 95 — 85 — 60 — 20 — 0 560 0 — 0 — 0 — 60 — 17.5 560 90 50 60 35 70 50 70 64 35 560 100 95 70 85 70 60 99 68

TABLE 94 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound BRAPP Compound BRAPP A Methyl Sulcotrione Ob Ex A Allyl Sulcotrione Ob Ex 4.38 0 60 — 4.38 0 80 — 8.75 0 60 — 8.75 0 100 — 0 70 15 — 0 70 70 — 4.38 70 60 66 4.38 70 99 83 8.75 70 85 66 8.75 70 100 100

TABLE 95 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Compound DIGSA A Methyl Pyriclor Ob Ex 4.38 0 40 — 17.5 0 50 — 0 140 80 — 4.38 140 99 88 17.5 140 100 90

TABLE 96 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weed in Direct Seeded Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound POLPY Compound POLPY A Methyl Glyphosate Ob Ex A Allyl Glyphosate Ob Ex 4.38 0 10 — 17.5 0 90 — 8.75 0 50 — 35 0 70 — 0 70 0 — 0 70 0 — 4.38 70 40 10 17.5 70 95 90 8.75 70 60 50 35 70 90 70

TABLE 97 Synergistic Activity of Herbicidal Compositions on Key Grass Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Compound DIGSA LEFCH A Methyl Glyphosate Ob Ex Ob Ex 4.38 0 0 — 20 — 8.75 0 20 — 30 — 0 70 0 — 20 — 4.38 70 60  0 50 35 8.75 70 80 20 40 44

TABLE 98 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Direct Seeded Rice % Injury Application Rate (g/ha) Compound CYPES CYPIR A Allyl Glyphosate Ob Ex Ob Ex 17.5 0 50 — 35 — 35 0 95 — 85 — 0 70 10 — 0 — 17.5 70 90 55 65 35 35 70 95 96 100 85

Evaluation of Herbicidal Mixtures for Weed Control in Transplanted Paddy Rice

Weed seeds or nutlets of the desired test plant species were planted in puddled soil (mud) prepared by mixing a non-sterilized mineral soil (28 percent silt, 18 percent clay, and 54 percent sand, with a pH of about 7.3 to 7.8 and an organic matter content of about 1.0 percent) and water at a ratio of 100 kilograms (kg) of soil to 19 L of water. The prepared mud was dispensed in 250 mL aliquots into 480 mL non-perforated plastic pots with a surface area of 91.6 square centimeters leaving a headspace of 3 centimeters in each pot. Rice seeds were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedlings at the second or third leaf stage of growth were transplanted into 650 mL of mud contained in 960 mL non-perforated plastic pots with a surface area of 91.6 cm² 4 days prior to herbicide application. The paddy was created by filling the 3 centimeter headspace of the pots with water. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-14 days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29° C. during the day and 26° C. during the night. Nutrients were added as Osmocote (17:6:10, N:P:K+minor nutrients) at 2 g per cup. Water was added on a regular basis to maintain the paddy flood, and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.

Treatments consisted of esters or salts of compound A, compound C, or compound D and various herbicidal components alone and in combination. For technical grade compounds, a weighed amount, determined by the highest rate to be tested, was placed in an individual 120 mL glass vial and was dissolved in 20 mL of acetone to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions obtained were diluted with 20 mL of an aqueous mixture containing 2.5% Agri-dex crop oil concentrate (v/v). For formulated compounds, a measured amount, determined by the highest rate to be tested, was placed in an individual 120 mL glass vial and was dissolved in 20 mL of 2.5% (v/v) Agri-dex crop oil concentrate to obtain concentrated stock solutions. The concentrated stock solutions obtained were diluted with 20 mL of acetone. Applications were made by injecting an appropriate amount of the stock solution into the aqueous layer of the paddy. Control plants were treated in the same manner with the solvent blank. All treated plant material received the same concentration of acetone and crop oil concentrate.

Forms of compounds A, C, and D were applied on an acid equivalent basis. Other herbicidal components were applied on an active ingredient basis and included acetolactate synthase (ALS)-inhibiting herbicides penoxsulam (triazolopyrimidine chemical class) applied as Grasp SC, pyrazosulfuron-methyl (sulfonylurea chemical class) applied as Sirius G, and bensulfuron-methyl (sulfonylurea chemical class) applied as Londax; acetyl CoA carboxylase (ACCase) inhibiting herbicides cyhalofop-butyl applied as Clincher G and fenoxaprop-p-ethyl applied as Ricestar HT; auxinic herbicide quinclorac applied as Facet 75 DF; phytoene desaturase inhibiting herbicide norflurazon; and p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting herbicide sulcotrione applied as Mikado.

The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.

Some of the herbicide combinations tested, application rates employed, plant species tested, and results are given in Tables 99-113.

TABLE 99 Synergistic Activity of Herbicidal Compositions on Key Grass Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound Bensulfuron- ECHCG ECHCO Compound Bensulfuron- ECHCG A Methyl methyl Ob Ex Ob Ex C Methyl methyl Ob Ex 8.75 0 0 — 0 — 17.5 0 0 — 17.5 0 0 — 25 — 35 0 10 — 35 0 25 — 20 — 0 35 20 — 0 35 20 — 20 — 0 70 45 — 0 70 45 — 30 — 17.5 35 40 20 8.75 35 40 20 35 20 35 35 45 28 17.5 35 55 20 35 40 17.5 70 60 45 35 35 60 40 50 36 35 70 55 51 8.75 70 60 45 40 30 17.5 70 65 45 55 48 35 70 80 59 60 44 Application Rate (g/ha) Application Rate (g/ha) Compound Bensulfuron- ECHCG LEFCH Compound Bensulfuron- ECHCG C TEA methyl Ob Ex Ob Ex A TEA methyl Ob Ex 35 0 0 — 50 — 35 0 20 — 70 0 25 — 95 — 70 0 50 — 0 35 65 — 15 — 0 35 65 — 0 70 70 — 30 — 0 70 70 — 35 35 90 65 85 58 35 35 95 72 70 35 95 74 100 96 70 35 99 83 35 70 80 70 90 65 35 70 100 76 70 70 95 78 100 97 70 70 95 85

TABLE 100 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound Bensulfuron- CYPES Compound Bensulfuron- ELOKU FIMMI A Methyl methyl Ob Ex C TEA methyl Ob Ex Ob Ex 4.38 0 0 — 35 0 0 — 0 — 8.75 0 15 — 70 0 50 — 0 — 0 4.38 40 — 0 35 20 — 10 — 0 8.75 50 — 0 70 70 — 50 — 4.38 4.38 85 40 35 35 50 20 0 10 8.75 4.38 75 49 70 35 60 60 40 10 4.38 8.75 85 50 35 70 80 70 40 50 8.75 8.75 85 58 70 70 80 85 100 50

TABLE 101 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound Pyrazosulfuron- ECHCG Compound Pyrazosulfuron- ECHCG A Methyl ethyl Ob Ex C Methyl ethyl Ob Ex 4.38 0 0 — 4.38 0 0 — 8.75 0 25 — 8.75 0 0 — 0 5.25 20 — 0 5.25 20 — 4.38 5.25 35 20 4.38 5.25 45 20 8.75 5.25 80 40 8.75 5.25 20 20

TABLE 102 Synergistic Activity of Herbicidal Compositions on Key Grass Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound ECHCG Compound ECHCG A Methyl Penoxsulam Ob Ex C Methyl Penoxsulam Ob Ex 4.38 0 0 — 4.38 0 0 — 8.75 0 25 — 8.75 0 0 — 0 4.38 70 — 0 4.38 70 — 4.38 4.38 90 70 4.38 4.38 95 70 8.75 4.38 95 78 8.75 4.38 70 70 Application Rate (g/ha) Application Rate (g/ha) Compound LEFCH Compound LEFCH A Methyl Penoxsulam Ob Ex C Methyl Penoxsulam Ob Ex 8.75 0 0 — 17.5 0 0 — 17.5 0 0 — 35 0 0 — 35 0 0 — 70 0 0 — 0 17.5 15 — 0 17.5 15 — 0 35 20 — 0 35 20 — 8.75 17.5 30 15 17.5 17.5 20 15 17.5 17.5 20 15 35 17.5 30 15 35 17.5 20 15 70 17.5 20 15 8.75 35 30 20 17.5 35 30 20 17.5 35 30 20 35 35 30 20 35 35 35 20 70 35 35 20 Application Rate (g/ha) Compound LEFCH C TEA Penoxsulam Ob Ex 35 0 50 — 70 0 95 — 0 8.75 0 — 35 8.75 80 50 70 8.75 100 95

TABLE 103 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound CYPES CYPIR ELOKU Compound ELOKU A TEA Penoxsulam Ob Ex Ob Ex Ob Ex C TEA Penoxsulam Obs Ex 35 0 20 — 10 — 30 — 35 0 0 — 70 0 50 — 20 — 20 — 70 0 50 — 0 8.75 40 — 70 — 0 — 0 8.75 0 — 35 8.75 60 52 100 73 60 30 35 8.75 60 0 70 8.75 95 70 90 76 80 20 70 8.75 80 50

TABLE 104 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weed in Transplanted Paddy Rice % Injury Application Rate (g/ha) Compound Cyhalofop- SPDZE C TEA butyl Ob Ex 35 0 50 — 70 0 80 — 0 90 0 — 35 90 70 50 70 90 95 80

TABLE 105 Synergistic Activity of Herbicidal Compositions on Key Grass Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound Cyhalofop- ECHCG LEFCH Compound Cyhalofop- ECHCG LEFCH A TEA butyl Ob Ex Ob Ex C TEA butyl Ob Ex Ob Ex 35 0 0 — 80 — 35 0 0 — 50 — 70 0 50 — 99 — 70 0 25 — 95 — 0 90 50 — 50 — 0 90 50 — 50 — 0 180 75 — 0 180 95 — 35 90 100 25 100 75 35 90 100 50 100 75 70 90 100 75 100 100 70 90 100 63 100 98 35 180 100 75 35 180 100 95 70 180 100 98 70 180 100 96

TABLE 106 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Compound Cyhalofop- CYPES CYPIR FIMMI SCPMA SCPJU A TEA butyl Ob Ex Ob Ex Ob Ex Ob Ex Ob Ex 35 0 25 — 10 — 0 — 0 — 85 — 70 0 50 — 20 — 0 — 50 — 95 — 0 90 0 — 0 — 0 — 0 — 0 — 35 90 100 25 40 10 40 10 10 0 100 85 70 90 100 50 100 20 100 60 100 50 100 95 Application Rate (g/ha) Compound Cyhalofop- CYPES CYPIR FIMMI SCPMA C TEA butyl Ob Ex Ob Ex Ob Ex Ob Ex 35 0 0 — 20 — 0 — 0 — 70 0 40 — 60 — 0 — 0 — 0 90 0 — 0 — 0 — 0 — 35 90 100 0 100 20 100 0 20 0 70 90 100 40 100 60 100 0 20 0

TABLE 107 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound Fenoxaprop- FIMMI SCPJU Compound Fenoxapro FIMMI SCPJU A Methyl p-ethyl Ob Ex Ob Ex A TEA p-p-ethyl Ob Ex Ob Ex 17.5 0 20 — 90 — 17.5 0 30 — 60 — 0 35 0 — 0 — 0 35 0 — 0 — 17.5 35 100 20 95 90 17.5 35 100 30 80 60

TABLE 108 Synergistic Activity of Herbicidal Compositions on a Key Broadleaf Weed in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound MASCR Compound MASCR A Methyl Quinclorac Ob Ex A TEA Quinclorac Ob Ex 17.5 0 0 — 17.5 0 35 0 50 — 35 0 60 — 0 140 0 — 0 140 0 — 17.5 140 40 0 17.5 140 80 60 35 140 60 50 35 140 80 60

TABLE 109 Synergistic Activity of Herbicidal Compositions on Key Grass Weeds in Transplanted Paddy Rice % Injury Application Application Rate (g/ha) Rate (g/ha) Com- Com- pound A LEFCH pound LEFCH ECHCG Methyl Quinclorac Ob Ex A TEA Quinclorac Ob Ex Ob Ex 17.5 0 10 — 17.5 0 10 — 10 — 35 0 20 — 35 0 15 — 80 — 0 140 0 — 0 140 0 — 0 — 17.5 140 20 10 17.5 140 60 10 100 10 35 140 45 20 35 140 70 15 100 80

TABLE 110 Synergistic Activity of Herbicidal Compositions on Key Sedge Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound CYPES FIMMI Compound CYPES FIMMI A Methyl Quinclorac Ob Ex Ob Ex A TEA Quinclorac Ob Ex Ob Ex 17.5 0 50 — 20 — 17.5 0 30 — 30 — 0 140 0 — 0 — 0 140 0 — 0 — 17.5 140 100 50 100 20 17.5 140 100 96 60 30

TABLE 111 Synergistic Activity of Herbicidal Compositions on Key Grass Weeds in Transplanted Paddy Rice % Injury Application Rate (g/ha) Compound ECHOR ECHCG A TEA Quinclorac Ob Ex Ob Ex 35 0 10 — 10 — 0 70 0 — 0 — 35 70 35 10 35 10

TABLE 112 Synergistic Activity of Herbicidal Compositions on a Key Sedge Weed in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound CYPES Compound CYPES A Methyl Norflurazon Ob Ex A TEA Norflurazon Ob Ex 35 0 60 — 17.5 0 30 — 0 70 0 — 35 0 70 — 35 70 95 60 0 70 0 — 17.5 70 50 30 35 70 100 70

TABLE 113 Synergistic Activity of Herbicidal Compositions on a Key Grass Weed in Transplanted Paddy Rice % Injury Application Rate (g/ha) Application Rate (g/ha) Compound ECHOR Compound ECHOR A Methyl Sulcotrione Ob Ex A TEA Sulcotrione Ob Ex 17.5 0 0 — 17.5 0 0 — 35 0 10 — 35 0 10 — 0 70 10 — 0 70 10 — 17.5 70 25 10 17.5 70 30 10 35 70 85 19 35 70 60 19

-   IPOHE=Ipomoea hederacea MASCR=Marsilea crenata -   POLPE=Polygonum persicaria POLPY=Polygonum pensylvanicum -   SPDZE=Sphenoclea zeylanica DIGSA=Digitaria sanguinalis -   ECHCG=Echinochloa crus-galli ECHOR=Echinocloa oryzoides -   ISCRU=Ischaemum rugosum LEFCH=Leptochloa chinensis -   CYPES=Cyperus esculentus CYPIR=Cyperus iria -   ELOKU=Eleocharis kuroguwai FIMMI=Fimbristylis miliacea -   SCPJU=Scirpus juncoides SCPMA=Scirpus maritimus -   Ob=observed values -   Ex=expected, calculated values -   DAA=days after application 

1-11. (canceled)
 12. A synergistic herbicidal mixture comprising an herbicidally effective amount of: (a) a first herbicide of formula (I)

wherein X is CH or N, hal is F, Cl or Br, and R is methyl or ethyl, or an agriculturally acceptable salt, ester or amide thereof, and (b) a second herbicide selected from the group consisting of: amidosulfuron, bensulfuron, bentazone, bispyribac, carfentrazone, chlorsulfuron, florasulam, flucarbazone, flufenacet, flupyrsulfuron, halosulfuron, imazamethabenz, imazamox, imazethapyr, iodosulfuron, mesosulfuron, metribuzin, metsulfuron, norflurazon, penoxsulam, pinoxaden, propoxycarbazone, pyrasulfotole, pyrazosulfuron, pyroxsulam, sulfosulfuron, thifensulfuron, tribenuron, and mixtures thereof.
 13. The mixture of claim 1 wherein X is CH, hal is F or Cl, and R is methyl.
 14. The mixture of claim 1 in which the pyridine or pyrimidine carboxylic acid of the formula (I) is a 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid derivative.
 15. The mixture of claim 21 in which the pyridine or pyrimidine carboxylic acid of the formula (I) is 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid potassium salt, or 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid triethylammonium salt.
 16. The mixture of claim 19, further comprising an herbicide safener.
 17. The mixture of claim 23 in which the herbicide safener is cloquintocet mexyl.
 18. The mixture of claim 19 in which the herbicide safener is mefenpyr-diethyl.
 19. The mixture of claim 19, comprising 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid methyl ester, pyroxsulam and cloquintocet mexyl.
 20. The mixture of claim 19, wherein the second herbicide is amidosulfuron and the weight ratio of the compound of Formula (1) to amidosulfuron is from 14:1 to 3.5:1.
 21. The mixture of claim 19, wherein the second herbicide is bensulfuron and the weight ratio of the compound of Formula (1) to bensulfuron is from 2:1 to 1:8.
 22. The mixture of claim 19, wherein the second herbicide is bentazone and the weight ratio of the compound of Formula (1) to bentazone is from 8.75:120 to 70:120.
 23. The mixture of claim 19, wherein the second herbicide is bispyribac and the weight ratio of the compound of Formula (1) to bispyribac is from 8.75:7 to 4.38:28.
 24. The mixture of claim 19, wherein the second herbicide is carfentrazone and the weight ratio of the compound of Formula (1) to carfentrazone is from 5:1 to 4.38:112.
 25. The mixture of claim 19, wherein the second herbicide is chlorsulfuon and the weight ratio of the compound of Formula (1) to chlorsulfuron is from 35:2.2 to 140:2.2.
 26. The mixture of claim 19, wherein the second herbicide is florasulam and the weight ratio of the compound of Formula (1) to flurasulam is from 112:1 to 8.75:1.3.
 27. The mixture of claim 19, wherein the second herbicide is flufenacet and the weight ratio of the compound of Formula (1) to flufenacet is from 17.5:15 to 70:15.
 28. The mixture of claim 19, wherein the second herbicide is flupyrsulfuron and the weight ratio of the compound of Formula (1) to flupyrsulfuron is from 28:1 to 7:1.
 29. The mixture of claim 19, wherein the second herbicide is halosulfuron and the weight ratio of the compound of Formula (1) to halosulfuron is from 35:26 to 8.75:52.
 30. The mixture of claim 19, wherein the second herbicide is imazamethabenz and the weight ratio of the compound of Formula (1) to imazamethabenz is from 140:125 to 35:125.
 31. The mixture of claim 19, wherein the second herbicide is imazamox and the weight ratio of the compound of Formula (1) to imazamox is from 70:22.4 to 8.75:22.4.
 32. The mixture of claim 19, wherein the second herbicide is imazethapyr and the weight ratio of the compound of Formula (1) to imazethapyr is from 2:1 to 1:4.
 33. The mixture of claim 19, wherein the second herbicide is iodosulfuron and the weight ratio of the compound of Formula (1) to iodosulfuron is from 35:3.75 to 56:1.
 34. The mixture of claim 19, wherein the second herbicide is mesosulfuron and the weight ratio of the compound of Formula (1) to mesosulfuron is from 140:3.8 to 35:3.8.
 35. The mixture of claim 19, wherein the second herbicide is metribuzin and the weight ratio of the compound of Formula (1) to metribuzin is from 70:50 to 8.75:50.
 36. The mixture of claim 19, wherein the second herbicide is metsulfuron and the weight ratio of the compound of Formula (1) to metsulfuron is from 140:3.75 to 35:3.75.
 37. The mixture of claim 19, wherein the second herbicide is norflurazon and the weight ratio of the compound of Formula (1) to norflurazon is from 1:2 to 2.38:560.
 38. The mixture of claim 19, wherein the second herbicide is penoxsulam and the weight ratio of the compound of Formula (1) to penoxsulam is from 8:1 to 1:4.
 39. The mixture of claim 19, wherein the second herbicide is pinoxaden and the weight ratio of the compound of Formula (1) to pinoxaden is from 70:7.5 to 8.75:15.
 40. The mixture of claim 19, wherein the second herbicide is propoxycarbazone and the weight ratio of the compound of Formula (1) to propoxycarbazone is from 140:15 to 35:25.
 41. The mixture of claim 19, wherein the second herbicide is a mixture of pyrasulfotole and bromoxynil.
 42. The mixture of claim 19, wherein the second herbicide is pyrazosulfuron and the weight ratio of the compound of Formula (1) to pyrazosulfuron is from 4.38:5.25 to 8.75:5.25.
 43. The mixture of claim 19, wherein the second herbicide is pyroxsulam and the weight ratio of the compound of Formula (1) to pyroxsulam is from 3.5:1 to 112:1.
 44. The mixture of claim 19, wherein the second herbicide is sulfosulfuron and the weight ratio of the compound of Formula (1) to sulfosulfuron is from 16:1 to 4:1.
 45. The mixture of claim 19, wherein the second herbicide is thifensulfuron and the weight ratio of the compound of Formula (1) to thifensulfuron is from 140:3.75 to 35:3.75
 46. The mixture of claim 19, wherein the second herbicide is tribenuron and the weight ratio of the compound of Formula (1) to tribenuron is from 35:3.75 to 140:3.75.
 47. An herbicidal composition comprising an herbicidally effective amount of the herbicidal mixture of claim 1 and an agriculturally acceptable adjuvant or carrier.
 48. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation an herbicidally effective amount of the herbicidal mixture of claim
 1. 49. A method for controlling undesirable vegetation in cereals which comprises: contacting the vegetation or the locus thereof with, or applying to the soil to prevent the emergence of vegetation, a mixture comprising an herbicidally effective amount of: (a) a first herbicide of formula (I)

wherein X is CH or N, hal is F, Cl or Br, and R is methyl or ethyl, or an agriculturally acceptable salt, ester or amide thereof, and (b) a second herbicide selected from the group consisting of: amidosulfuron, bensulfuron, bentazone, bispyribac, carfentrazone, chlorsulfuron, florasulam, flucarbazone, flufenacet, flupyrsulfuron, halosulfuron, imazamethabenz, imazamox, imazethapyr, iodosulfuron, mesosulfuron, metribuzin, metsulfuron, norflurazon, penoxsulam, pinoxaden, propoxycarbazone, pyrasulfotole, pyrazosulfuron, pyroxsulam, sulfosulfuron, thifensulfuron, tribenuron, and mixtures thereof.
 50. The method of claim 56, wherein the cereal is rice. 